Secrets to Driving High-Conversion Inbound Leads

*Editors Note: Recaps and slide decks from the Sales Hacker Series – Hacking Lead Gen in Toronto are brought to you by Third Core. Third Core designs and executes repeatable, predictable sales strategies for technology companies all over North America. Follow us @Third_Core.

This session is titled Secrets To Driving High Conversion Inbound Leads by David Priemer, VP Sales, Salesforce.


Top 3 lessons learned about Sales

  • Selling stuff is hard
  • People operate on inertia and its hard to change the status quo
  • Only your mom thinks you are smart

You have to break the Intertia (ie. people doing the status Quo)

  • Reduce friction in the sales cycle to make it easy to buy
  • Generate high intent leads to minimize the amount of work required in the sales cycle

Increase the amount of high intent leads using messaging that is:

  • Polarizing- People get it quickly
  • Relevant- Message hits home
  • Insightful- Teaches people something


*Read Robert Cialdini’s “Yes! 50 Scientifically Proven Ways to Be More Persuasive”


Questions to ask when developing polarizing messaging

  • What BIG problem are you tackling?
  • What universal issue are you improving?
  • Who specifically your solution targets.

Examples of polarizing messaging

  • “Sales rep attrition costs your company millions”
  •  “Happy customers are your best sales people”
  •  “Accounting software for non-accountants”

Questions to ask when developing relevant messaging

  • Is your customers pain part of your message?
  • Are you focused on the right roles/people?
  • Are the words you’re using the right ones?

Use mirroring to use the right words in your messaging

  • Listen to the words your customers use when talking about their challenges and use them in your messaging

Provide insight during the sales cycle

  • Leverage the power of reciprocity. People are more likely to buy when they feel they owe you something
  • Use insights to uncover hidden pain



  • Use messaging that is polarizing, relevant, and insightful to drive high intent leads
  • Disrupt interia to drive high intent leads
  • Use mirroring to ensure you use the same language as your prospects




Sales Hacker Series Toronto was Sponsored by Third CoreToutAppSales For Life, and Influitive.

How Your Customers Are Your Best Sales Channel

*Editors Note: Recaps and slide decks from the Sales Hacker Series – Hacking Lead Gen in Toronto are brought to you by Third Core. Third Core designs and executes repeatable, predictable sales strategies for technology companies all over North America. Follow us @Third_Core.

This session is titled Your Customer Are Your Best Sales Channel by Emmanuel Skala, VP of Sales, Influitive.


Buyers are in control, salespeople need to adapt

  • Use an advocate network to ensure prospects have access to positive endorsements early in the cycle
  • Make advocate enlistment a high priority activity in your company
  • Ask advocates to review you on social pages, review sites, etc.

**Read Geoffrey Moore’s “Crossing the Chasm”- good read Don’t be old school

  • Traditional approach says not to introduce referrals until prospects are close to close
  • Better to introduce referrals early in the cycle when prospects are the most unsure
  • 4.2 x higher probability of closing a deal when using advocacy 

Be a “matchmaker”

  • Introduce advocates that have similar roles and responsibilities to your prospect
  • Frame introduction so it is beneficial to both parties, not just you

Delight your customers

  • Get to know them through sales cycle, send them a gift when the deal closes
  • 60% of Brand Loyalty is based on sales process

Take advantage of the honeymoon period

  • Soon after closing the deal ask customer for a referral. Who do they know that might benefit from the same solution? Who do they know that has the same challenges? 

The Influitive Sales Process Connect

  • Hack #1- Build Personal Brand, Get Advocates to Review you
  • Hack #2-  Be a matchmaker with your prospects

Educate – 75% of Sales Process

  • Hack #1-  Get advocates to give you reviews
  • Hack #2-  Rethink references- give them earlier!


  • Hack #1-  Delight with gifts and insights
  • Hack #2-  Ask for referrals from new customers

  Three times to ask for referral 1)      Disqualified-  They cant use your product or service but is there anyone in there network that can 2)     After the Deal is closed 3)     When the customer received value from Product / Service Close the loop

  • When someone gives you a referral provide them an update on how the sales cycle is progressing


  • Begin to build a culture of advocacy with your customers
  • Go and ask your customers whether they are willing to provide references a few times a month, provide them value for doing so (ie. introduce them to people they value meeting)
  • Introduce referrals earlier in the cycle by being a matchmaker
  • Connect, educate, and delight!



Sales Hacker Series Toronto was Sponsored by Third CoreToutAppSales For Life, and Influitive.

Social Selling Tips for Lead Generation

*Editors Note: Recaps and slide decks from the Sales Hacker Series – Hacking Lead Gen in Toronto are brought to you by Third Core. Third Core designs and executes repeatable, predictable sales strategies for technology companies all over North America. Follow us @Third_Core.

This session is titled Social Selling Tips for Lead Generation by Jamie Shanks, Managing Partner, Sales for Life.


How to monitor your account base 

By tracking who has bought from you in LinkedIn you can get alerts when they change organizations. Get in touch with them and see if they will buy in their new position.

  • Advocates are 6X more likely to buy!

How to Track Buyers on LinkedIn

  • Go to LinkedIn Advanced Search page
  • Enter company name of current users of your product/service in Boolean format (Oracle OR ADP OR Bank of America). Set status to “past not current”
  • Enter the titles you sell to in Boolean format (VP of Sales OR VP of Marketing OR CFO). Set status to current
  • Save search in top right corner, add title and choose how often you want to receive updates
  • Every time someone changes company you receive an update and can follow up to see if they will buy in their new position

Blind Connections DO NOT WORK

  • Make sure you share some commonalities with a prospect
  • Groups offer endless prospects

Get free mail when you share groups

  • Find prospect you want to connect with
  • Look at the groups they are in. If you share a group you can send free INmail
  • INmail response rates are 7x higher than regular email
  • Groups also expand your search when looking for prospects, join the maximum number of groups you can
  • Contribute to groups and become ranked, provides visibility in large groups


  • Track all of your current buyers on Linkedin to ensure you can connect with advocates that change organizations
  • Share common groups with prospects so you can send direct messages

Be active on Linkedin and prepare a routine of checking updates and reminders, and follow up with people who change jobs or get promoted



Sales Hacker Series Toronto was Sponsored by Third Core, ToutApp, Sales For Life, and Influitive.

A Simple Management Technique to Score More Goals, in the World Cup and Sales

Editors Note: Guest post by contributor James Pember. James is the CEO of Sparta Sales, a platform that helps sales teams drive competitions in order to boost sales, motivation and energy.

With the World Cup currently taking the world by storm and the semifinals coming up today, I’ve thought a lot about how football managers motivate their players to reach their full potential – and what sales leaders could learn from this.

Did you happen to see the epic finish to the Brazil/Chile game a few nights ago, in which Brazil stole the game away from the Chileans in a penalty shootout? After seeing that, I decided to take a deeper look at how football manager’s motivate their players to take those shots under extreme pressure, and how sales leaders can use similar tactics to motivate their teams to smash their targets.


How motivational language affects performance

A pair of researchers (Heidi Grant Halvorson and E. Tory Higgins) wrote a fantastic book on motivation called Focus: Use Different Ways of Seeing the World to Power Success and Influence. For all sales managers, it’s definitely worth picking up – it’s a relatively easy read and definitely includes a lot of actionable insights.

During their research they studied professional football players in Germany and how they responded to motivational pressure from their coaches. Specifically, they studied how different motivational language would affect different personality types and their hit rates during penalty shootouts.

Example 1. Promotion vs Prevention

One of the core concepts outlined in the book is that there are essentially two different types of people, when it comes to motivation – those driven by promotion and those driven by prevention. As I’m sure you can guess, those characterized as “promotion-types” are driven by hitting goals and progression, whilst those “prevention-types” are driven are more focused on safety and maintaining the status-quo or even just keeping their job.

Study: German football players and motivation

Now, as I explained – the study was focused on German football players and how motivational language would affect their performance. The team was split into two groups – “promotion-types” and “prevention-types”. The players were to take 5 penalty shots on goal.

The coach then told the promotion-types:

“I want you to put at least 3 or more into the net”.

The coach instructed the prevention-types:

“I want you to NOT miss two, or more”.

Then, to control – a separate group of players were given the opposite instructions, according to their “motivation type” (prevention vs promotion).

As you can see, everyone is being told the same thing – score 3/5 shots, however – the language is very different. The promotion-types are driven by hitting a goal, whilst the prevention-types are given a very different type of motivation, almost a “do not fail” type of message.

So, what happened?

Well, the results were fairly interesting. If you were a promotion-type player, you scored more goals if you were given this goal-orientated promotion language. If you were prevention-type player, you scored more goals if you were given the don’t miss, don’t-lose-prevention language.

Motivating Salespeople: Language

So, let’s say two salespeople have a target of $80,000 per month. Your promotional-type sales rep probably thinks something like this:

“Let’s crush this target and get to $150,000!”

On the other hand, the prevention-type will be thinking:

“Ok, I need to bank one $20k deal per week to make sure I’m OK”

Here’s the thing though – perhaps the best sales reps should be promotion-types driven by targets and recognition? Another book (Drive by Daniel Pink) explores exactly that – that bonuses and promotions work extremely well on salespeople and not say, software engineers for exactly that reason – that salespeople are fundamentally driven by recognition and hitting goals.

Now, that’s not to say that those goals and rewards have to be financial, in fact – there has been plenty of research that has shown financial incentives are not as powerful as non-financial – but the fact remains the same, great salespeople are driven by hitting targets.


I’m sure you have a mix of “prevention-types” and “promotion-types” in your organization – so it’s critical that you tailor the messages and goals accordingly. Perhaps your first task is to uncover what motivation type your reps are in the first place, then you can start working on how you set goals and use motivational language in order to get the most out of your team.

Good luck!

4 Data-Driven Hacks to Find Your Real Ideal Customer Profile

Editors Note: Lincoln Murphy is the Customer Success Evangelist at the leading Customer Success SaaS company, Gainsight. He’s helping drive Gainsight’s thought-leadership in the areas of Customer Success, retention, churn mitigation and expansion revenue. He also writes about all things SaaS at Sixteen VenturesThis is the first article in his new ongoing series on Customer Success Hacks exclusive to


When I help Enterprise SaaS companies accelerate their sales process, one of the first things we do is create an Ideal Customer Profile. In my experience, having a very specific customer you’re marketing and selling to just makes things easier.

It makes things easier for you because you know how to reach them where they are and you know what to say that resonates and compels them to take action (rather than trying to strong-arm and convince random people).

It makes things easier for your customer because you’re speaking their language while talking about the problems/opportunities that are acute in their world. They don’t have to use a lot of cycles to get from the conversation that’s going on in their minds to how your product will fit in with that. You’ve done that for them.

But to me, defining an Ideal Customer goes way beyond just figuring out what I’m going to say to a prospect or put in an ad. When you really get into this process, you’ll figure out how to get customers that will get you more customers. And how to get customers that will pay you more to use more of your product over time.

These four Ideal Customer hacks I’m going to share with you could – if you’re open-minded – completely change the way you decide who you want your customers to be.

And that could completely change your business!

Ideal Customer Profile Framework

My Ideal Customer Profile Framework ( I suggest you spend some time studying this) was created – and is always evolving – to give my clients and me a simple method upon which to build our ideal Customer hypothesis.

This framework consists of 7 inputs – all dictated by the situation for which we’re identifying the Ideal Customer – and those are:

  1. Ready
  2. Willing
  3. Able
  4. Successful
  5. Profitable
  6. Expansion Potential
  7. Advocacy

It should be obvious that if you can find a prospect who is Ready, Willing, and Able to become a paying customer, that’s a great start.

But… if that customer is more likely to be successful with your product, you can acquire and support that customer profitably, there is expansion potential there, AND they’ll be an advocate for you… now that’s definitely an Ideal Customer!

In the Ideal Customer Profile Framework, I talk about how everything is situational. That could mean you’re trying to identify an Ideal Customer for your company overall, or a specific campaign you’re running. Which means, you may wish to pull this data within a certain contract value in mind, those that had a < 30-day sales cycle, or those that came in via a certain marketing channel.


Your Data-Driven Ideal Customer Profile

Below are four “data hacks” you can use to really find just those customers that are going to be awesome for you.

Whether you have a full-blown Customer Success Management platform (full disclosure: I work at Gainsight, a vendor in the CSM space) or you need to pull this together from disparate systems. If you’ve been in-market for a while, you should have this data somewhere.

Okay, here we go…


Ideal Customer Hack #1: Identify Your Most Successful & Healthy Customers

The idea here is simple… your Ideal Customers are more the ones most likely to achieve success with your product.

There are some very simple things you can do to ensure you go after customers that can be successful with your product, and that is to be honest about the technical/infrasture/data requirements to be successful.

For instance, if you have an app that runs natively in, while you may be able to work with other CRMs, the likelihood of success is greater if you target customers already using Makes sense, right?

Okay, so beyond the technical requirements, now we want to find your customers with the highest average lifetime Customer Health Score – meaning they didn’t just achieve a high Customer Health Score two-years into their contract with you, but were healthy from the beginning and kept that up over time. And then we’ll look for patterns.

If you don’t have a Customer Success Management platform yet (you should, BTW), an actual Customer Health Score may be hard to find – especially historically – so you’ll pull together other data points to try to come up with your own “Customer Health” score.

For instance, you could pull together average Net Promoter Score (NPS) over time, on-boarding/implementation milestone data, Common Conversion Activities data, Customer Support data, and maybe get your Account Managers to apply a “health” score – based on their gut – to each of the customers they manage. Sure, a real CSM solution could give you this report quickly, the point is even without that you should be able to get this data.

Okay, so what are the patterns that seem to lead to success? You have to consider all aspects of on-boarding, customization, data seeding/cleansing, etc. as well as technology/infrastructure requirements.

Is there an industry, company type or size, or revenue amount that appears to be more successful (healthy) than the others? Did the companies that found success buy through a VAR? Was an internal champion present?

Understanding what goes into making your customers successful will surface ideas on what to look for in prospective customers…. assuming Customer Success is a goal of yours (and it probably should be).


Ideal Customer Hack #2: Identify Your Most Profitable Customers

Look, the definition of – or even the need for – profitably acquiring and supporting a customer changes depending on your company stage and goals. Because of the deep dependence on the situation, I won’t spend a lot of time here except to say that acquiring customers has a cost and you may want to make sure you recoup that cost as quickly as possible. Maybe.

That cost is generally referred to as Customer Acquisition Cost (CAC), and should be “fully loaded” including all the costs to advertise to, sell to, support during a Free Trial or Proof of Concept, and convert to paying customer.

If the sum of all that is less than the profit you get from them over some pre-determined time-frame (we’ll say in the first 12 months), then you can say that you’ll acquire them profitably.

But CAC isn’t the only cost you need to be aware of in figuring out the “Profitable” input for your Ideal Customer Profile. The immediate-post-sale costs such as on-boarding, provisioning, data cleansing/seeding, customization/configuration, training, etc. needs to be figured in. And then the ongoing cost to support regular use, like Infrastructure costs or Customer/Technical Support.

And frankly, the difference between you skating by on razor-thin margins or living large with super-fat margins ultimately comes down to the customers you acquire. That determines whether they’ll pay the premium price, whether their support costs are too high, their CAC is too high, sales cycles are too long, their customization/integration needs are too high, etc.

Again, you can look to your CSM solution to figure out all of this, or pull the data from the myriad customer data systems you have. Maybe look for customers that had a short sales cycle, have a high LTV with long-term contracts but increase usage frequently and have a low cost to support.

What are the patterns? What are the characteristics of those customers? Now we’re starting to paint a picture of an Ideal Customer!


Ideal Customer Hack #3: Identify and Exploit Expansion Potential

This is what I refer to as Intra-Company Virality and provides you with tons of opportunity for Up-Sell and Cross-Sell within the same company.

One of the questions I hear all the time from startups is “should we go after Enterprise or SME customers?” Well, it’s usually in the form of a statement about who they’re targeting, which is always both SMEs and Enterprises… which means they don’t “target” anyone. Fail!

Now the real answer to the question – target Enterprise or SMEs? – has many inputs, not the least of which are sales cycle length, deal size, etc.

But one input that few really consider is the Expansion Potential of the account.

If you sell to a company with 25 employees and they buy 25 seats and have 100% usage, how do you expand the account? How do you grow revenue? You better have additional features or non-user-based usage fees you can charge, right? Because if you wanted to add just 1 more user, the company would literally have to grow by 4%.

But if you sold that same 25 licenses with the same usage, into a department/org in a large Enterprise, if you wanted to grow the account by 1 user, they’d just add a user. The department growing by 4% is nothing. A rounding error.

Couple that with other departments that are interested in what you have (which happens even more and a lot faster when you fully orchestrate this process; the “virality” piece I mentioned), and there is a ton of expansion potential.

Maybe the sales cycle will be longer for the initial Enterprise-focused sale (though if you do things right you can accelerate this significantly, especially in this land-and-expand fashion), but the long-term growth after the initial sale might just make it worthwhile.

And you should be able to gather from your Customer Success Management system a list of companies that have expanded their use over their lifetime with your company… what are the patterns and common characteristics? Who did you initially sell to? What department/persona?

The “Ideal” in Ideal Customer is really starting to shine through now, right?

Before we move on, I just have to make sure we’re clear on this. When it comes to expansion potential, that potential is only recognized when the customers have achieved success… when their customer health score is high.

No Customer Success.. no expansion revenue. Period.


Ideal Customer Hack #4: Leverage Your Network of Advocates

I think of Advocacy as Inter-Company Virality… it’s how boring ol’ B2B products “go viral” and it’s how you can leverage your focus on Customer Success to drive Second Order Revenue by having your customers bring you more customers.

I said this recently on Twitter… chasing logos is fine… but chase logos that’ll bring you more logos!

And the only way Advocacy happens is if customers are finding success with your product. If they’re ever going to be an advocate for you, it’s when their Customer Health Score is high.

No Customer Success… no Advocates. And no “viral” growth.

So use your Customer Success Management solution to look for customers that have been your biggest advocates. If you’re measuring correctly this should include those who have referred new customers through their use of your product (think: they send a file, the recipient gets the file but also becomes a user and then a paying customer), have given testimonials, have talked to prospects on your behalf, etc.

While you may not WIN the deal because of the advocacy of your customers, you may be IN the deal because of it. Don’t underestimate the value of Customer Advocacy.

When you pull this data on your biggest customer advocates – again, ensuring other situational parameters are set, too – what patterns emerge? Types of customers? Size of customers? Industry? LTV?

Now you take that Advocacy data and use that input in your Ideal Customer Profile and all of the sudden you have an amazing picture of your absolute Ideal Customer.


Don’t let FOMO Derail You

Now, a lot of folks are afraid of narrowing things down to one Ideal Customer – even if just for a single campaign – and that’s due to FOMO (the Fear of Missing Out).

They think that if they focus on only one type of customer, they’ll miss out on all the rest. But the reality is, when you don’t focus, and instead try to be everything to everyone, you end up making a connection with no one.

And when that happens, I guarantee you’re missing out. And to make matters worse, because you’re talking generically (probably about your product instead of them), you’re actually missing out on the people who are, in fact, your Ideal Customers.

So go develop your Ideal Customer Profile now, then go identify companies that match that profile, and then figure out how to get in front of them with the right offer at the right time; for the win.

How to get a Stranger to Agree to Something

*Editors Note: Guest post by Andrew Fogg, co-founder and Chief Data Officer of a free tool that allows you to transform the web into a table of data or an API quickly and easily without having to write any code.*


Getting a stranger to agree to something is all about negotiation. Whether you realize it or not, you negotiate every single day. We are all in the business of motivating people to do things for us; whether this be motivating your team to pull together, motivating your customers to buy from you, or motivating investors to give you money.

Now, I’m no expert at negotiating. In fact, when I first entered the business world I was pretty bad at it. Luckily for me, negotiation is a skill, and like any other skill it can be learnt and practiced. So, I read lots of books by experts and did some of my own on-the-fly experimenting. Through study and practice, I was able to teach myself to be a better negotiator and now I want to share with you a few tips and tricks that you can use to improve your skills.

In this post I want to run quickly through how to deal with three negotiation scenarios that are specifically relevant to sales and startups, all of which come from my own personal experience.


Getting a Meeting (Networking)

If you want to get a meeting, the first thing you need to do is to articulate – to yourself – who it is you want to meet. I don’t necessarily mean that you need to know their name, although of course that helps, it is more about knowing the profile of the person that you want to meet.  What is their job title? What is their role in the organization? How are they going to help you?

If you’re targeting a specific person or organization, the first step is always LinkedIn.  Even if you aren’t connected to them directly, you may know someone who knows that person and can introduce you. Introductions are key. A good email introduction lends you credibility, makes people far more likely to agree to meet with you and will make them generally more receptive to what you have to say.

Introductions are karma – give them away and they come back to you. If someone asks you for an introduction to someone that you know give it with generosity!

If you’re targeting lots of people, ask yourself where those people go online and in real life. Then, find those places, go there and join the conversation. When you’re networking in real life, just go up to people, stick your hand out and say hello. Drink, if it’s offered, but don’t get drunk. I’ve seen this go badly for people before!

When you get to the point of actually scheduling a meeting here is a crucial time saving tip: send a calendar invite directly.  Then send an email saying that you’ve sent a calendar invite. Nine times out of ten you will have hit an empty spot in their calendar and you just eliminated the back and forth of emails trying to find a time when you are both free.


Getting a Deal (Sales)

Most of my experience is around selling to businesses, so I’m going to focus on that. There are really only two ways to sell to a business: you either help them save money or make money. It is better to help a business to make money.

If you’re helping a business make money, there are generally two ways to get them to actually buy from you.  One way is to identify a budget that you are targeting that is being spent elsewhere and claim it as your own. This means that the customer does not have to go and find new budget for your new product or service, they just redirect existing budget. The other way is to insert your product into the customer acquisition process. If you can do this, then the value proposition to the customer becomes a matter of a simple formula: more money spent with you = more revenue generated for me.

As a technology startup you may be approached by big consultancies or Systems Integrators who will offer to help you find clients. Don’t do it. In my experience, this nearly always ends up being a waste of time. It is busy work. You will spend lots of time in meetings discussing potential leads and business opportunities and it feels productive but chances are that it will not go anywhere. I think that one of the reasons for this is that consultancies are in the business of building things, and in the back of their mind they’re always thinking “we could build that”.

Be confident when it comes to pricing. Remember that you’re selling value to the customer.  The cost to you of generating that value is largely irrelevant. Practice value-based pricing. Also, be creative and confident when it comes to payment terms. Ask for payment up front for example, or for longer terms even if your service is meant to be sold via a monthly recurring fee.


Getting a Contract (Negotiation)

Paperwork!  If you do not have contracts yet then go get some. You can of course pay a lawyer, but there are plenty of contracts online that you can look at and amend to suit your needs. When it comes to signing paperwork, everyone wants to sign on their own paperwork (including you), so get your paperwork issued first and you are more likely to be able to make that happen.

Contract negotiation takes time and I would argue that it generally adds very little value to the deal itself.  By the time that you get to the point of issuing contracts the major fundamentals of the deal will have been agreed by all major stakeholders. All that is left are general boilerplate terms, which – while they are important – do not need to be negotiated with every single customer. If you send a contract out as a Word document you are guaranteed to get a redline in return with a bunch of suggested changes that will pull you into a contract negotiation.  My advice therefore is to never send out a Word contract again.  Instead, issue a simple one-page order form (as a PDF) that references an online master agreement that has all of the general terms.  This reduces the likelihood of getting into negotiations with your client’s legal or procurement department.

Of course you won’t always be able to avoid contract negotiation. You will get proposed changes back. Some you are going to be ok with and some you are not going to be ok with. When you get proposed changes back, in the first instance, dispute them all (even the proposed changes that you are ok with). This achieves two things. Firstly, it allows you to discover the changes that the customer really cares about. They will likely easily concede the changes that they don’t really care about. Secondly it gives you some changes that you can easily concede in return for gaining concessions from the customer on the changes that you really care about. Finally if you get stuck on a clause that seems unfair, it is worthwhile suggesting that the clause is made symmetrical so that the provisions apply to both parties.

The most important thing is to keep the momentum of the deal going; so reply quickly to emails and phone calls. Be prepared for the fact that enterprise sales can be a long process.


I threw one last one in here, which is for everyone.  It’s a favorite of mine and something that you can do almost anywhere.


Getting an Upgrade

I try to get an upgrade whenever I hire a car, take a flight, or check into a hotel. The first thing to do is to smile and be courteous. Service staff often have to deal with people who are in a rush or sometimes even angry, so if you are nice to them, they will notice. Remember to use their first name when addressing them and try to get them to laugh or smile. If you can get them to laugh or smile in the first 60 seconds then you are well on your way to building genuine rapport. Be sincere and enjoy getting to know the other person. Taking a genuine interest in people is the most natural thing in the world, and people can always tell when you are faking it.

Once you’ve built rapport, you can ask them the killer upgrade question that will deliver the goods: “Is it a good room?”, “What kind of cars do you have?”. Ask the question in a way that will prompt the other person to think about it and they will give you a better option if they can.
And that’s all there is to it!

Below is the presentation I gave at the London Hacker News event. Video can be found here.


How Salespeople Should Be Thinking About Emails

The world of sales is undergoing a massive transformation with all the new advancements in sales technology, but one thing that has remained consistent over the past few decades is the use of email.

Before email existed people wrote letters. Therefore, when email took off, people continued to write emails in the format that they would write letters. Well, letters have been on a steep decline in the business world and even the personal world for quite a while now. The only time I put something in an envelope is when I need to mail a check. Even then, I am silently shaking my head at the recipient who is clearly behind the times by requiring me to write them a check, instead of being able to pay them instantly with the many available online and mobile payment products that exist today.

So that brings me to my next point. Why are we still writing emails like we’re sending letters? I don’t know about you, but one of the most prevalent mantras I’ve heard as a salesperson from other salespeople is, “make emails short and concise so someone can read it with the flick of their thumb on their smartphone”.  Ok, that sounds like a text message, right? Then shouldn’t our emails start taking the form of texts and not letters?

Switching from “Letters” to “Texts”

Why are we still signing off on emails in an email thread? No point of saying “Best”, “Cheers”, “Thanks”, etc at the end of an email in an email thread anymore. The only time it’s not useless is when you are specifically demanding or asking for something or intending to end the conversation/thread. “Let me know” and “Please advise” are also unnecessary because a good email implies a response is required. The easier you can transition an email conversation from a back and forth “letter” feeling to a “text” feeling, the better you can build a rapport.

Always use the “hi and bye” in an email to someone you’ve never spoken to before. Feel them out before you take it to a more casual place. After a few emails with the same person, there’s no need to say Hi {name} anymore either.

Knowing Who They Are

Social channels like Twitter are a great way to find out how someone likes to interact with others. Look at what they’re talking about and how they like to talk about it, and then build a rapport with them through that.

For example, If someone seems stiff and “old school” you may want to stick with the letter style emails until you warm them up. If someone is talking like a “bro” about startup acquisitions or sports, you can approach more casually.

The more you can find out about them, the easier it will be to motivate them and the better equipped you’ll be to interact with them and remind them of a place of trust. Social selling is not just about context or Why You, Why You Now (see John Barrows & Jeff Hoffman), which is great and incredibly helpful, but it’s also about understanding how they like to interact with others. This will help you understand who they are to the world and how they express themselves. This is how you take things to the next level.

Social Cues and When it’s OK to Use That Smiley Face

I was recently talking with Scott Britton about Social Calibrations, or the psychology behind how people interact through email. I’ve recently been thinking about this offline too and will follow up in a separate post.

The question really is, how do you know when it’s ok to start using that exclamation point or that smiley face? Some would say it’s never OK, but I think that’s a dated way of thinking because we’re moving these emails to a “text” format, not “letters”. I almost always like to make the other person be the first to use an exclamation point or smiley face. You would never want yourself to look amateurish or less professional because of a gaff like that. However, if you have the dominant hand, you can write however you’d like. If Richard Branson responds to your email, he can ;-) at you all day long. As the more junior in that situation, you would let him make the first move before returning serve with a ;-) of your own. Mirroring through email is a great way to continue building rapport. Just make sure you know your position and if you’re the lower in rank, let them make the first move. The only time I break this rule is if I need to change the attitude in the conversation and even then, it’s rare.

An example of this would be where someone makes a big ask and there’s no way we can oblige. Judging by the tone of the ask, I can tell if they’re shooting for the moon and know we can’t make that happen, or if they actually think that it is a reasonable ask. If I know it’s the former, I can respond with something along the lines of “as much as I’d love to provide all that value for you, we just wouldn’t be able to make it happen because it would interfere with XYZ and neither of us would benefit from that :-)” (use a scapegoat, never take blame, but never deflect to an individual, only on to something bigger than both entities or something intangible. More on this in a future post.)

Using the exclamation point too often or too quickly can also be seen as eagerness or over appreciation, thus giving the person on the other end a thought that they are doing you a service by conversing or indulging you. This is why you want to be careful about your position. If in anyway you can possibly be seen as equals or lower by the other person, don’t use the exclamation first, unless you need to turn the conversation around.


  • Sales is evolving into a mobile first world. Shouldn’t email evolve with it?
  • Start forming emails like texts, not letters. But use proper english and don’t talk like a 13 year old on a Kik messenger.
  • Use social to help you understand how your email recipients interact with others.
  • Be aware of the wording and emails you’re sending and how they can help you build a rapport.
  • Use mirroring in emails. As they get more casual, so can you. Abide by the exclamation and smiley face rules.

Listen, I’m not saying we shouldn’t have manners. We should always be respectful and say hello and goodbye when it’s the right time to. My point is, why say it constantly in the middle of a conversation? Let your email threads flow and create a warmth around your conversation and it’s participants.

Agree or disagree? Let me know in the comments and please add what industry you’re in and what the customer profile of who you’re selling to looks like.

Sales Hacking Bootstrappers Guide – Deep Dive #2- Stop Pitching

*Editors NoteGabe Luna-Ostaseski is a serial entrepreneur and founder of Calfinder and Upshift Partners. They help small startups scale sales teams. This article was previously posted on the Upshift Partners blog and is being republished with their permission.*

If you’ve been following my posts here on the Upshift blog, you know that: 1) I posted a detailed guide giving away my trade “secrets” for succeeding as a bootstrapped business, and 2) it was so well received that I decided to go into more detail on the points presented in response to your comments. You can read my first deep dive on the 80/20 rule which addresses many of your questions about how to identify your best customers and create more of them. Here, I’ll be focusing on your questions about how to get new customers without ever doing a sales pitch again. (Okay, I’ll admit, that’s a “buzz” term my marketing folks want me to use to get your attention. I don’t necessarily think there’s anything wrong with a “sales pitch,” it’s just that so many of them suck that it’s given the whole concept a bad rap. So for the purposes of this post, forget about pitching.)

How did you grown your business from $2,000 to $2,000,000 in sales in just four months without pitching your product?

I provide great detail into how I accomplished this in my first post in this series, the Bootstrappers Guide. Here, I’ll tell you that I had a lot of doors slammed in my face along the way. Like I said, the idea of a “sales pitch” has a bad connotation. What I’m proposing, simply put, is, rather than go in with your sales pitch, offer something of value before asking something from the other person. Interesting idea, huh? Just a slight reorientation of your intention can shifts the dynamic a little bit, hopefully a lot. We hear sales pitches everywhere we go, and we get immune to them. We cringe at the sound of anything resembling a “pitch.”

Don’t get me wrong, the entrepreneurs out here in Silicon Valley are selling the vision for their companies to the VC’s on Sandhill Road every day and raising millions of dollars in the process. Are they doing it with a sales pitch? Maybe. But I’ve seen that the ones that are getting money are the ones that are educating and solving problems, not selling.

The Takeaway: Don’t pitch your company/product/idea; rather educate your prospect. Discover their pain point and tell them how your company/product/idea can help.

It can be so demoralizing when you gear up for a big pitch and don’t get the business. Any tips on how to handle this and keep knocking on the doors?

Doors will get slammed in your face. I know, I literally had my nose pressed to thousands of them when I went door-to-door over a series of summers while building my first business. You need to develop a thick skin. Those entrepreneurs that develop that skin and keep going are the ones that have built really successful businesses. If you can walk around and get used to doors being slammed in your face, congratulations, you’re an entrepreneur!

In more practical terms, if you spend one-half hour with a customer and don’t close the sale, ask yourself:

  • Have you educated someone about your industry or product?
  • Have you helped them in some way?
  • Have you left an impression?
  • Have you built trust and respect?
  • Have you made a connection that could potentially call you in six months, should their circumstances change?

The takeaway: If you can walk away from a meeting believing that you’ve accomplished at least one of these points, it wasn’t an unsuccessful sales meeting. Develop thick skin.

I find it hard to work on pitching my business or raising funds when I’m still ironing out our product and dealing with the day-to-day issues that come up. Can I delegate this to someone else?

It depends on what stage your company is in. For early stage companies, you as the founder absolutely should be involved in the marketing and sales of your company. You need to hear firsthand the feedback that’s coming in on what you’re putting out there so you can work to make improvements.

There are other things that you can find others to do, like operational tasks. Find someone you trust to handle opps and focus your energy on how to get customers.

The takeaway: No matter how great your product or idea is, you won’t go anywhere with it if you don’t get yourself some customers.

In your Bootstrapping Guide, you talk about continually following up with prospects with calls and gifts every week. How adamant are you about these “stalker” tactics?

Pretty adamant. That’s because I’ve seen the payoff. There’s a fine line between being persistent and being an asshole that no one wants to talk to. Obviously, I’m recommending the former. By repeatedly sending key prospects something funny or clever, eventually they realize you’re serious. So even though nothing might typically happen the first few times, it’s that one golden moment when the CEO of a prospect company calls and says, “Okay, you’ve got my attention, what can you do to help me? — that makes it all worth it.

The takeaway: Calling and pestering doesn’t accomplish anything. But if you really think about how to stand out when you’re making those calls, then you’ll get noticed.

Okay, so if I’m going to be a stalker, do you recommend a specific time of day or week or days to reach a contact by phone, email, social media?

Companies have to discover this for themselves, but what’s key here is that most entrepreneurs don’t take the time to try different tactics and track what’s working. An early stage company, in particular, should be reaching out to prospects at different times of the day, and different days of the week, and measuring the success rates of each tactic. The results might be one thing for a healthcare company versus a SAS company or a BtoC company, so try different things and see what works the best.

A later-stage company should have a more sophisticated CRM tool in place that records the highest response rates for email, phone calls, etc.

The takeaway: Take a step back, look at your results, see which 20% is working best (see more about this in my post on the 80/20 rule), and then refine your strategy.

Can you share some examples of offers that have worked for you in the past?

Again, what worked for me may not be exactly what works for you. But I’ll tell you what we did for my marketing consulting company that brought in new business.

We sent prospects:

  • A $2 bill

With the tag line: This $2 bill is magical; it multiplies when you spend it on generating more traffic to your website.

And the solution: Let us prove it to you.

  • A sticky hand

With the tag line:  Are you concerned that your marketing programs aren’t sticky enough?

And the solution: Call us we’ve got some great glue!

  • A flying pig figurine

With the tag line: The only time your conversion rate will increase is when pigs fly.

And the solution: Unless you call us!

  • A pen with a flashlight –

With the tag line: Do you feel in the dark about how your marketing results are going?

And the solution: Give us a call; we’ll help shine a light.

There were a lot more but you get the idea. We sent one of these little gifts in succession every week; some funny, some compelling, but always with a message that showed we were serious.

The takeaway: In all of these cases, the key was to think about the pain point they have and how our service addressed it, but in a fun and clever way. (Okay, maybe cheesy in some cases you might think, but it worked.) Think about what will work for your business.

So, why are you giving away all of your trade secrets?

I’ve done this already; I’ve built my businesses and I wish that someone had given me this kind of advice when I was coming up. I’m not saying my process is the be all and end all; just that it worked for me. There are lots of ideas out there but what makes the best ones rise to the top is testing and execution. I like to drill it all down into a step-by-step process, learn what works and what doesn’t, and try to adopt the things that work. A lot of this basic information was missing when I was started out; I sincerely want to help others avoid the same mistakes I made.

It’s important that new ideas get out there. That’s what my current company,Upshift Partners, is all about. We at Upshift want to see companies succeed; we want to see entrepreneurship thrive. Our core mission is to help increase the success rate of startups. And to do this, we are continually learning, uncovering new concepts and ideas that help the companies we incubate. We’re out there trying to improve our program and learn from the companies we work with so we can help them and others succeed. So I guess that’s why I’m really doing this.

What else would you like to know about the sales pitch or any other part of the startup process? Leave a comment below and I’ll either get back to you here, or address it in an upcoming post.

Building Massive Lead Lists Through Outsourcing

*Editors Note: Live updates from the Sales Hacker Series – Hacking Lead Gen in New York City are brought to you by Betts Recruiting. Betts Recruiting helps companies teams staff and attract talent for all revenue generating roles. Follow us @BettsRecruiting.

This session is titled Building Massive Lead Lists Through Outsourcing by the CEO of LeadGenius, Anand Kulkarni 

How you should think about growth

Once you have product market fit, the only acceptable limits on your sales are:

  • not enough leads at the top of the funnel
  • not enough sales people to close the deal

Growth Talking Points

  • How to get sales people to pitch out to 50-100 extra people a day
  • How to automate this process


What Sales Used To Be

  • Hire a giant SDR staff
  • Buy a canned list
  • Work your way down that lead list with cold calls

Sales is Now Hypertargeted

  • Find and rank every potential qualified customer in the entire country (with no developers!)
  • Figure out relevant data about each of those customers
  • Write each one of those customers a personalized message from a salesperson


Why go virtual?

In house SDR – in SF

  • $80,000K per year plus benefits
  • Slow to hire
  • Competitive to retain

Virtual Staffers

  • $10-20/hr
  • Endless supply
  • Dedicated and happy – working from home

How to set up a Virtual SDR team


  • Craigslist
  • oDesk/Elance
  • Freelancer
  • Jobs Board


  • TaskUs
  • LeadGenius

Best practice for setting up virtual SDR Teams

  • 1 lead gen staffer
  • 1 outreach staffer
  • 1 manager/QA (!!!)


Setting up your lead list

There are 21 million businesses, 6 million with more than 1 person.
Your customers are listed in

  • Yelp (47M establishments)
  • LinkedIn(2M companies)
  • Crunchbase(650K companies)
  • Angelist(289K companies)

Start by searching and segment your lists

  • State by State
  • City by Sity
  • Vertical by Vertical

Avoid low quality sources like and Dunn and Bradstreet. Old and expensive data. Plus, people on those lists are getting cold emailed all the time.

Helping out your virtual SDRs

Researchers should have access to

  • Linkedin Premium
  • Google Spreadsheets
  • Rapportive
  • Toofr (verification)

Prospectors should have access to

  • Linkedin Premium
  • ToutApp, Yesware, or Streak
  • Salesforce/CRM access


Pitching Leads

Use a virtual assistant – give them templates to use that they can personalize based on specific directions.  It needs to be custom, personalized and relevant.

Check their LinkedIn profile, recent funding, any public information on them or their company.

  • Interested – here are 3 times that work for me
  • Check back later – Automatically schedule a follow-up mail
  • Specific question – Here’s more info

Measuring your ROI – is very important!

You have to be able to see what is working and what isn’t.  So always be tracking…

  • Cost per lead
  • Leads per week
  • Emails per week
  • Converations

What numbers should you expect?

10 leads per hour, 10 custom emails per hour, 10% response rate

Cost per message is $1-2, $20 cost per lead, $80-200 per closed deal.


  • Don’t do this inhouse
  • Generate massive lists of leads
  • Prospect short and sweet and until pipeline is full
  • Monitor ROI obsessively

Resources, Tools, and Tactics to Hack Lead Gen on the Cheap

*Editors Note: Live updates from the Sales Hacker Series – Hacking Lead Gen in New York City are brought to you by Betts Recruiting. Betts Recruiting helps companies teams staff and attract talent for all revenue generating roles. Follow us @BettsRecruiting.

This session is titled Resources, Tools, and Tactics to Hack Lead Gen on the Cheap by the CEO of Sales Hacker Media, Max Altschuler

Companies with low budgets are paying for leads and its expensive and the data is old. You especially shouldn’t be doing at a startup, or at a company of any size.  More and more people are starting to build for salespeople. Take advantage of this.

Along with the new sales tools, leverage outsourced help. It can be really cheap  and you don’t have to pay for zoominfo or

Lead gen strategy:

  • Figuring out your ideal customer profile and where to find them
  • Top down and Bottom Up outreach
  • Mix of web scraping, Virtual Assistants, and Sales Automation tools
  • Customize the entire process up until prospects first response
  • Use free and cheap tools

You have to have an idea of what companies you are selling to and who you are selling to.  If you are in the email marketing field – these people are already customers somewhere else, you just have to find them. You the Market Share data for free at Datanyze to help see the industry leaders.

Ideal Customer Profile: ICP

  • Who is your target user, customer, company?
  • Where are they, what products are they using, what are they paying for?
  • Use Datanyze, BuiltWith or Mixrank to find customers that are already using other products
  • Reverse engineer existing deals to figure out your target job title you should be going after and segment that by the size of the company. At a F500 company it’s different than at a 20 person startup.

Now that you know who you’re targeting, start building lists.

Web scraping tools

  • Kimonify

For sales conferences, you can take companies that are sponsoring similar events and put them into a spreadsheet quickly and easily. Once you already have column A, your team can get to work find email addresses.

All you need is a link to somewhere where you know your ideal customers are. Scrape that and you have a start to your list. If you can automate this process it saves tons of time.

List building


  • All you need is first name, last name and domain – you can pull out names by the thousands
  • Can pull accurate lists in real-time by the 1000s


  • All you need is title or company name
  • Test emails directly into your browser
  • Can pull .csv files of massive, targeted lists

Using a Virtual Assistant you can find 60-80 emails an hour. These emails are targeted and fresh.


ToutApp (which Max uses)
Signals by Hubspot

  • Take the leads lists and upload them into ToutApp.
  • create a template and A/B test 4 subject lines if you have 1000 addresses.
  • Run A/B test for call to action.

Using this method you will find the highest open and click through rates and which subject lines and calls to actions work best.


  • Use virtual assistants and pay them $3-$5 an hour
  • Have them create a Google Group to self train and self manage
  • Create very detailed directions with screenshots for training.
  • Put a test in the job description.


  • Teach entire process to a VA team
  • Get them to build lists and send emails for you
  • You take over as soon as a lead responds
  • Set up a call on the first response
  • Great for companies with endless leads
  • Can be done with a 1 man team or large sales org

Good startup CRMs

  • RelateIQ
  • Pipedrive
  • Base
  • PipelineDeals


  • Bigger companies should check out TaskUs/LeadGenius
  • Followerwonk for finding individuals with certain skillsets in their Twitter bios, etc
  • Keyword SEO tools for creating keyword strings for your VAs (
  • SellerCrowd for finding the right targets in Brands and Agencies
  • Rapportive,, Boomerang for Gmail, Google Labs for Gmail (Undo Send)

Follow Max @MaxAlts

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