3 Pieces of Advice for Emerging Sales Leaders

*Editors Note: Recap post of the Deck presented at Sales Hacker Series in Boston on November 18th, 2014 by Devon McDonald, Director of Growth Strategy at OpenView

1. Sending Daily & Weekly Updates 

There is something to be said about sending a daily update to stakeholders within your business with what you accomplished that day. It sounds a little bit crazy, right? We live in the day of automated reports where Salesforce can send your manager your output / activities for the day, but it’s extremely beneficial at the end of the day to reflect upon what you did, what you accomplished, and where you stand against your goals.

But more importantly, what is the context of the conversations you are having with your buyers? From those daily updates you can pull that contextual information and share it with your team(s).

The Context

  • What are Buyers Saying?
  • How are they Responding to Messaging?
  • What are their Objections?
  • What Content are they Asking for?

As a sales rep, particularly if you are a BDR, you’re having more conversations than anyone in your business with your target buyers. That’s gold. Companies that recognize that Inside Sales teams and BDRs are a huge asset to their business are the ones that end up being the most successful.

A lot of that information the reps hear, and sometimes they’ll put it in Salesforce but it doesn’t always make it up to the top, to the people that really care about that stuff. So we have our BDRs (and remember, these are often people that are fresh out school) we have them sending daily updates to their CEOs. Now, that seems a little crazy and probably pretty scary but from what we’ve seen this is gold. They want to see this!

As a result of doing this, other teams in the company get very curious about the conversations that you’re having. The marketing teams should be heavily involved so they can create around the objections sales is getting and where people are getting stuck around the messaging.

Simple Daily Update Email:

Daily Update Email

2. Don’t Treat Marketing Like The Enemy

There is still a ton of tension between sales and marketing. If reps and managers do what they can to help bridge that gap, everyone is going to be better off. Take initiative with marketing and share with them on a regular basis what you’re hearing from prospects and what is / is not resonating with them. To take is a step further, ask marketing what you can do as a sales rep to help. Marketing teams at startups are strapped for time and it can be a very thankless role. Offer support in whatever way you think you could be valuable. Even if they don’t take it, you will still be seen as a team player and future leader.

Now, you obviously have a busy schedule so you can’t take on writing eBooks for your marketing team, but perhaps there are little things that you could do that show that you care. Again, you’re having tons of conversations with the target audience, so if you enjoy writing offer to write a blog post. Little things like that can be extremely helpful.

Share your feedback on the content they are providing you (regardless of your seniority level):

  • What are you hearing from prospects?
  • What is resonating?
  • Where are your leads getting “stuck”?
  • What do you need more of?

Send a recap of your conversation with the marketing team and let them know what you think would be beneficial to the sales team. Mark the Marketer – “Great catching up today. I appreciate all that you do for our sales team and getting us great content!”

3. Have a Plan for Yourself

Where do you want to be in the long-run? Now, don’t come in week 2 on the job and say “I’m ready for a promotion. I’ve nailed it.” Once you’ve proven yourself (i.e. 2-3 quarters of consistently hitting your goals) bring visibility to your manager as to where you want to be eventually and ask what it will take to get there. Don’t expect it to happen over night, but work with your manager to develop a roadmap to get to that end goal… even it’s a multi-year plan.

When you plant that seed in your managers head to where you want to go, so when that opportunity does come up for organizational changes you will be top-of-mind (especially if you’ve taken the previous two pieces of advice above).

Again, after you met with your manager – document it.

Manager Follow Up

Your managers are busy, just like your marketing leader was, and they might not remember everything you talked about. Give a recap. Too, your manager may have said things to you:

  • “Yes, I want to help you get there.”
  • “Yes, let’s do this.”
  • “Yes, you can get there in the next two years.”

Put that in writing and get them to respond to it. Save it for the future because this stuff will come back to help you.

Bonus: Find the answers to your own questions

Use the resources at your finger tips. Could the answers to your questions easily be found on:

  • Your wiki?
  • Your training docs?
  • Your website?
  • GOOGLE!?

Can’t find your answer after all that? Save a list of the questions you need to ask your manager for the end of the day.

You must self-educate. Don’t expect to be coddled.

  • Read books and top sales/marketing blogs
  • Attend networking events and meet-ups – good job, you are already doing this!
  • Find mentors/coaches who you can turn to for advice
  • Attend events that are relevant to your buyers and the industry you sell into – without being asked, and potentially without being sponsored
  • Take classes outside of work that are relevant to the role you eventually want to be in

For more Sales Hacks Follow us on Twitter at @SalesHackerConf

Be Yourself with Video Selling

*Editors Note: Guest post by Sati Hillyer, Founder and CEO at OneMob. Sati is a seasoned entrepreneur with startup and big company experience that is transforming an idea into an established company.

Unless you’ve been hiding under a rock, it’s impossible to miss the impact video has had on us. YouTube is the world’s second largest search engine. Why? Simple, people enjoy watching videos more than reading text. It’s in our DNA, 93% of human communication is visual and vocal, so text alone will never be as captivating.

Yet, sales are still primarily done through emails and documents.

Think Differently, Use Video to Sell

After being inundated with hundreds of text-based emails and numerous unsolicited calls, it’s refreshing to see someone take the time to record a personal message. It’s like receiving a handwritten thank you card. Sending a personal video does a few things:

  1. Increases Engagement: Videos increase email open rates by 2x and click through rates by 15x.
  2. Increases Trust: Putting a face to a name shows the prospect you are NOT a robot and helps build trust (it’s much harder to ignore someone who shows more effort).
  3. Increases Conversion: Videos are captivating and fun to watch. With more watches, you can expect a 5x increase in response rates because your message is now finally being heard.

Sales in the past was face to face because you had no other option. Sure it took longer, but it was incredibly effective when building trust and establishing a longer term relationship. Let’s face it, today’s emails and phone calls are cold, face-less and suspicious. Even with powerful marketing automation tools, it’s so easy to come off as a robot to your prospects.

How to Sell with Your iPhone Camera Right NOW

Using the forward facing camera and holding your iPhone landscape (watching videos in portrait suck), you can get started right now. The initial experience is similar to recording your first voicemail, so I recommend following these tips:

  1. Have a Script: Don’t just go off the cuff. Instead, have an idea of what to say and practice it a couple times first so it comes off naturally.
  2. Keep Steady: Instead of holding the iPhone, use a tripod or lean it against the laptop screen and position at eye level. This allows you to focus on your delivery and keep from shaking.
  3. Have an Ask: After you introduce yourself and explain why you’re reaching out, be sure to end with an ask such as leave a response or schedule a time to meet.

Here’s an example to see what the end result can look like:

Be Yourself with Video Selling


Sales is a numbers game. Prospects and customers are drowning in their inbox and it’s difficult for the sales person to stand out, be remembered and ultimately get a response. A short, personal and professionally branded video is the perfect hack to improve your sales. OneMob makes sales personal and fun again with the power of video, and the 5x increase in response is well worth it. Contact us to take advantage of our launch special. Happy selling!

Negotiating & Objection Handling

*Editors Note: Guest post by Ben Sardella, Co-Founder at Datanyze. This blog post is a recap of the Deck he presented at Sales Hacker Series in San Francisco on October 23rd, 2014. SlideDeck is viewable below.

The relationships we have with our clients are cultivated for a very long time. Negotiations are a mutual agreement where both parties feel like they got something out of the deal and you don’t “win” a negotiation by making the other person lose. So as you approach your negotiations make sure you’re approaching them with a win-win attitude, especially if you’re in the SaaS space.

Think: When does the negotiation process actually begin?

When you take a step back and think about negotiations, it’s really all about qualification. When you qualify a deal the right way from the start you know where the negotiations are going to be headed when it’s time to talk about price, contract terms, etc. You also will know what objections that might come up.

A “Mutual Action Plan” can kickstart the negotiation process by simply coming to an agreement on the series of events and common interests.

Think: How would you buy from yourself?

If you haven’t thought about that as a salesperson, you should probably stop and think through how you’ve purchased software for your organization, or you’ve seen members of your organization purchase some solution of service, ask them how they went about that process. That’s really going to give you some insights how your own customers are buying from you.

Build a buying process map with the knowledge that you have of buying services yourself, as well as how your customer’s have purchased in the past, looking at what it takes to make buyer make that final decision to work with you and what steps they take along the way is critical for your success as a salesperson.
Too often we build a sales process to match our goals that we need to close a deal, instead of mapping that to the goals that align with our buyers. Taking the steps to build a buying process map will give great insights on when and what the negotiations and objections will be.

Take it a step further by creating a buyer persona map that has targeted messaging, benefits, and expected objections. For example, a CEO is going to have different objections that a VP of Sales, or the VP of Marketing, etc. So aligning what you feel would be the benefits as well as the objections that are going to come up from these individuals as you interacts with them during the process is really key to understanding what pitfalls you may run into and how the conversations are going to go.

4 Typical Objections

1. Not interested / Resistance to Change

This is one of the most difficult, but most common objection that we deal with when we try to sell. But the reason that this comes up in a lot of cases is that we likely did not qualify properly. They’re telling you “There just isn’t enough pain, and the status quo is perfectly fine with that”

In this scenario, the next steps to take are asking probing questions to uncover areas of pain that you’ve seen from similar customers. Get into an agreement that if they were to solve their pain points they’d be able to see some ROI in a given time, then they would be interested in making that change sooner rather than later.

2. Need to Get Approval / Not the Decision Maker

You’re not dealing with the decision maker. So in this case ask the right questions to get in front of the decision maker early. If someone is dragging you along and you’re not talking to an executive thats going to sponsor this project, you’re likely to have a long and dragged out sales cycle. In the end, it may never get in front of the person that you need to engage with.

Don’t tie yourself just to the end user, also think about the overall value that the company is going to get to overcome the objections that executives may have.

3. Timing

When that happens it means that we haven’t established the cost of doing nothing yet. They probably like your service but there is just no immediate urgency for it. So understanding the short term and long term goals of your customer is really important in this case.

A lot of times if you’re in SaaS, you could ask “What if I offered you this product for Free, and started to charge you in 2 months. Would you close the deal then?” If it’s a “yes” just not right now then challenge the buy by offering flexibility in your contract terms such as a free month or lower monthly costs to start at the beginning of the term.

Asking questions like that will help you figure out what is really important to them right now.

4. Cost / Lack of Budget

There’s never been once when there wasn’t enough budget to address the pain we had, or for a customer to buy something to address a pain that was immediate and urgent.

Haven’t established ROI/value above status quo/current pain (remember, budget always exists if the pain or return is too great to ignore). To overcome this by getting back to the value you provide and the cost of not selecting your service.

Also, target those areas where those budget dollars are being spent for the same results. For example, if you’re selling into marketing, chances are they’re spending budget on content. Leverage your service to help them out in those areas.

5 Most Important Questions to Ask to help lower barriers (e.g. objections) in future negotiations
If you won:
      1. What events happened recently that led up to the purchase?
      2. When did this happen?
      3. What made you choose us?
      4. How could we of made it easier to become a customer?
      5. Do you know anybody who has gone through the same events recently that could use our service?
If you lost a deal or lost a customer:
      1. What events happened recently that led up to the purchase/decision?
      2. When did this happen?
      3. What made you choose our competitor over us?
      4. How could we of made it easier to choose us (or less likely to leave us)?
      5. Do you know anybody who has gone through the same events recently that could use our service?

Take findings from questions and do a force field analysis from deals won and deals lost – focus on reducing common barriers/objections for future deals.


Learn more about the next Sales Hacker Series meetup on Negotiation & Objection Handling  in New York City this Thursday!

Sales Hacker Series - New York City - Negotiations & Objections

How InsightSquared Generated 3X More Meetings in One Day

*Editors Note: Guest post by Steve McKenzie, VP of Sales at InsightSquared. Join him and other Sales Hackers on Tuesday, November 18th in Boston. Learn more about the event

If you were around the InsightSquared office last Monday, you would have seen capes and masks and lots of Spandex. Halloween wasn’t for another week – what was going on?

Welcome to the InsightSquared Superhero Call Blitz, an initiative designed to give the team – and the sales pipeline – a shot in the arm. For one full day, each member of the sales team – from the VP of Sales and the Sales Director to the Business Development Reps – got on the phones and dialed, dialed and dialed some more. I even joined in for part of the day, though a few people didn’t believe the CEO was calling them. The results?

3X more meetings booked than our typical day.

With numbers like these, maybe more CEO’s should ditch the suit in favor of a Captain America bodysuit, rippling muscles included.

The Method Behind the Madness

The team didn’t just decide to dress up as Robin and The Punisher, and then book more meetings. No, this was a concerted plan that started with the leadership team, and was then executed by the team through sheer dint of human effort.

“This was designed to give our team and pipeline a shot in the arm,” said Steve McKenzie, InsightSquared’s VP of Sales. “We wanted to take what we normally do but flip it on it’s head. The day was designed to be a high-octane, high-energy day where everybody’s attention and focus are all heightened. I think it worked very well.”

The day started with a team breakfast, followed by an impassioned motivational speech from McKenzie, aka Mr. Incredible. After that, as soon as the clock struck 8:00 am, the entire team – including Steve and I – got on the phones. The costumes continued to play an integral role as well; reps who mentioned they were dressed as Batgirl or Black Widow found great success and made their prospects laugh with their icebreakers.

“It was important that everyone dresses up and we all feel a little silly,” said McKenzie. “We chose superheroes because we knew the team would deliver a superhuman effort, and we wanted that reflected in reality. When you’re all wearing a cape or a muscle-bound suit, you feel silly, but also a little more confident.”

While the results and sales metrics were great, Steve also found the whole experience of living in his reps’ shoes for a day to be invaluable. It’s very easy for a Sales VP or a sales manager to direct reps to make a certain number of calls and activities each day; it’s much harder to maintain the discipline to execute that on a day-to-day basis.

McKenzie found himself taking more time to prepare for calls than his reps typically would. Working at his pace, the reps would never be able to hit their daily activities quota. This led to Steve questioning the merits of measuring reps on the activity-based KPIs.

“It’s easy to dial; it’s much harder to talk,” said McKenzie. “I’m more interested in the quality of conversations than a rep who makes 150 calls but has maybe only 1 or 2 decent conversations.”

Is this sustainable?

Unfortunately, probably not. As great as the one-off results were for this Superhero Call Blitz, we were well aware of the unsustainable nature of this exercise. For starters, the reps would likely keel over in exhaustion – making 177% of your daily calls is no small feat, and not easily repeated.

Additionally, normal activities were held off in favor of just calling as many names as possible. Instead of taking high-quality inbound leads from marketing, reps had to set up their own lists, drawing from long-dormant names, closed-lost leads or just cold calling new names altogether. Typical sales processes – like email check-in and scheduled call-backs – were eschewed. The sales managers had to make sure there was a clean plan for following-up on the successful connections from the Call Blitz, with the standard process having been thrown to the wind on this day.

There’s also the matter of getting buy-in from the entire team, especially mid- and senior management members. Marketing chipped in to organize breakfast, set up decorations and judge the costume contest. The Sales Director – who hadn’t prospected in years – contributed 5 meetings booked on his own. Without planning and full buy-in from all participants, the day would not flow properly and would not be very effective.

Despite the aforementioned unsustainable elements of the initiative, the Superhero Call Blitz was nevertheless an immense one-off success. Morale was improved, the energy in the sales pit was positively buzzing, the sales reps enjoyed the experience of their managers getting in the trenches with them, and of course, the team booked 3x the number of meetings they typically did.

All in a day’s work for Superman and his friends.


Check out the eBook: The Definitive Guide to Building a Prospecting Team by InsightSquared and join Steve McKenzie at the Sales Hacker Meetup in Boston on November 18th at OpenView!


The 10 Key Revenue Mistakes I Made Getting to $100 Million ARR

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled The 10 Key Revenue Mistakes I Made Getting to $100 Million ARR, by Jason Lemkin of SaaStr, Echosign, and Storm Ventures.

As you scale your SaaS companies, if you avoid these mistakes you will be much more successful.

Mistake #1: Not Hiring 2 Sales Reps

You will easily learn what you are looking for in your top sales rep if you have someone that’s number 2. 1 rep performing is repeatable, and 2+ Reps Performing is repeating.

You have to sell it yourself first, and then hire 2 reps. Be sure to hire a marketing manager before a sales manager.

Mistake #2: Hiring Early Reps I Wouldn’t Buy From

You will need many types of reps eventually, but in the early days leads are precious. You won’t feel comfortable handing your leads off to someone you don’t trust. If you wouldn’t buy from them personally, don’t hire them. Another good rule to follow when hiring your first sales reps, make sure they have at least 2 years of experience in SaaS.

Mistake #3: Not Seeing the Pattern Early Enough

The pattern is set early, and there is often a natural pattern between customers. You’ll realize that you have an “organic” type of core customer. Once this is repeating, be confident. Don’t be afraid to double down on what seems to be working. While deal sizes, etc will go up, the pattern that has established itself will stay the same. Keep at it, it will keep working.

Mistake #4: Not (intentionally) Going upmarket faster

Nothing is an anomaly. If you can get one enterprise customer, you can get 10. Realize that the outliers aren’t anomalies, they are the future. If you can go up-market, go up-market faster.

Corollary: Go upmarket as soon as you can. You will get more money for the same work.

Mistake #5: Not Seeing the Power of a Mini-brand

Brands are highly defensible. When people in your core industry are starting to notice you, your brand becomes incredibly powerful. It tends to happen when your brand becomes repeatable. Invest in your mini brand, even if you don’t see direct ROI. Do as much as you can to build trust of your product. You also must have some competitive advantage in the marketplace, focus on it and build it up.

Mistake #6: Ever Allowing Revenue per Lead to Drop

Revenue per lead should never drop. There is something wrong here and you have got to fix it. This may be a time to focus on PR, marketing, upgrading the team or more customer success. Competition should not be a factor here. It is everyone’s fault if you are losing revenue on leads.

How did Brendon double sales in 90 days?

  • Immediately upgraded the team to proven closers
  • Got the most out of the team he inherited-and got rid of the ones that weren’t working
  • He did not attempt to do it alone
  • He ended pipeline as a metric

Mistake #7: Too much time on prospects v. Existing

Sales is just the start of a 5-7 year journey. Visit all of your top customers, not just prospects. Pay attention to upsells and upgrades, and try and get more out of existing relationships. If you develop a good relationship with them, they will take you with them wherever they go. We never lost a customer we visited. Get on a plane and visit all your best customers, and all your top 20% customers. ALL of them. Even happy customers will churn if you don’t visit them, and on the flip side, unhappy customers will still stay if you visit them. In typical enterprise relationships, you typically lose a customer in year 3. Year one it is in the budget, year 2 already has the deal legacy built in from a budgeting perspective, year 3 is when they start making changes.

Mistake #8: Not Firing a Bad VPS in 1 Sales Cycle

70% of businesses hire the wrong VPS at first. You should know subjectively in just a few months, just 50% of the way through your average sales cycle if you have hired the wrong person. Numbers should increase in one sales cycle, with keen focus on revenue per lead. This increase does not even need to be significant, but with the stuff in the system, there should be at least SOME improvement in sales. The first few hires your VPS makes should be clear upgrades and made quickly and seemingly effortlessly. If you hire the wrong VPS, they will hire subpar people below them. This can be fatal.

Mistake #9: It gets SO much better at Initial Scale

No matter how bad you are at X, or inexperienced at Y, you will learn in SaaS. Training gets better, script gets better, as well as the process and journey. While it may not get easier, it does get better, and you get better. Find a way to get to $10 million. $1m to $10m tends to be the toughest slog.

Mistake #10: Not Doubling the Plan

Once the team was finally great, we exceed the plan. Every quarter, every year, always. I wish I would have challenged us to do better than 120% of the plan. Imagine a world where capital doesn’t matter, where you can hire whomever you want, and were ROI can be measured in 36 months. The great will never propose something stupid in this scenario. Find out what it would take to get to your goal, then go find a way to make it happen.

The First Order of Business for a new VP of Sales

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled The First Order of Business for a new VP of Sales by Brendan Cassidy, VP of Sales at TalkDesk.

 Three things to understand when you’re about to enter a start-up:

  1. It’s going to be hard.
  2. Be flexible.
  3. Most cannot do what you are endeavoring to do.

Step 1 – Establish the True Lead Velocity Within the Business

  • You don’t know anything until you understand your lead velocity
  • Questions to ask
    • Is there someone running marketing?
    • Is there established criteria around what a lead is?
  • If someone is running marketing, and you align with their definition of an MQL, the model should be fairly easy to build.
  • If there is no one in marketing, then you need to define what an MQL is and then retroactively assign an MQL status to every lead that came in for the last three months. Once you’ve weeded out all the non-MQL’s, you’re at a true north point from which to scale the business.

Step 2 – Once lead velocity is established:

  • Structure the sales organization based on the data, not on what you’ve done in the past.
  • One common mistake that VPs of Sales do is they try to replicate exactly what they’ve done in the past

Step 3- Put in the playbook. Hint: Keep it Simple

  • You are making your customers lives easier. Not harder. Sell accordingly.
  • Make the pricing easy to understand and transparent
  • Sell to your strengths
  • Understand your weaknesses. Make sure your sales people understand your weaknesses. Make your weaknesses a strength
  • Understand how your competitors are attacking you

Step 4 – Hire the Best Talent. Period. (That’s on YOU)

  • Common mistake with the first time VPs of Sales – hiring good, smart talented people as long as they’re not smarter than you. Get past your own insecurities. If you hire someone smarter than you, that’s a good thing.
  • Try to hire your core, early team from within your extended network. Not your first 2 or 3. Your first 10.
  • Why? Because you reduce risk if someone is vouched for by people you know? Your best hires are going to come through your network. Period.
  • If you don’t have a network. Start now. Today. It will pay off later.

Step 5 – Always seek solutions. Not excuses.

  • You weren’t hired to tell the CEO why it can’t be done
  • If there are no leads, then you need to build an aggressive outbound sales development organization. Maybe even 1 to 1 SDR to AE. And it’s not going to be cheap.
  • If you do have some lead velocity, identify exactly how many leads you need marketing to commit to in order to scale to 10, 20 , 50, 100 sales people. This is easy to model.
  • If the product doesn’t work, help your CEO recruit the right engineering.

Step 6 – Pay your sales people above market rate for performance.

  • Hiring great talent is hard
  • Retaining great talent is even harder
  • If you are cheap, you’re dead. Period.
  • You can do all of this and make sales an accretive profit center, not a cost center.

Step 7 – Promote from within

  • Build a meritocracy. If you want your top performers to stay with you through multiple stages of growth, give them a path to realize their ambitions.
  • Remember – the folks that build your team own the intellectual capital. Bringing in a sales executive might work, but it won’t ultimately help you scale.

Step 8 – Have fun!

  • 70 to 75% of your life and time will be spent working. Try to make it as fun and rewarding as possible.

What I Learned Scaling From 2 to 80 Salespeople in Under a Year

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled What I Learned Scaling From 2 to 80 Salespeople in Under a Year by Sam Blond, VP of Sales at Zenefits.

There were many things we learned along the way that took us from 2 to 80 Salespeople in under a year, and today I will share some of those with you.


  • What to look for in a rep:

Look for synergy between what they have done in the past and what you are doing. Make sure they have seen an early stage startup and can make an impact without having to invest extensive training.

When you bring on new sales reps, remember hitting numbers should be a definition of success. For myself, I always shot to be number one. When I look for candidates I see how they rank against their peers. If they aren’t number one, are they passionate about being number one, or do they show the desire to improve?

Finally, always ask for 5 references. Anyone can find 3 people to speak positively about them. Once you dig into number 4 and 5, you tend to get more accurate and complex information. It helps to position it as, “We are thinking to hire John, what can we do to help make him successful?” This leads the way for their references to surface any weaknesses that may change your hiring decisions.

  • When is it time to hire a VP of Sales?

First, get a few sales reps and a million in revenue. You want to find someone who will be a good leader but also have the right amount of talent. The VP should also collaborate well with the existing team.

  • When should you use Outside recruiters?

In the beginning, outside recruiters can be very helpful in helping you generate a pool of candidates with the right talent. Use a variety of recruiters for diversification.

  • When should you hire an internal recruiter?

If you are hiring 2-3 people a month, it is probably time to hire an internal recruiter.

Quotas and Compensation-

Quotas should be challenging, but attainable. A good goal is to set your quota so 70% of your sales reps can hit it.

Remember, you get what you pay for. Be more aggressive on the variable compensation side and aim for above the market rate. Make people want to work for you, then you can be selective when hiring.

Controlling cycle times-

Controlling your cycle time is incredibly important because if a sales rep is taking extensive amounts of time to close an opportunity, they are unable to focus on new opportunity and you are missing out on revenue.

The role of discounting will play largely into this. Be creative with how you position offers. What we did, is every few months we would tell customers we were losing the ability to discount and they needed to take advantage now.  You must be creative in your approach.

Finally, don’t back down. Don’t extend a discount or offer, they will usually end up closing anyways. If you say yes, they will have that expectation in future negotiations.

Specialization and sales development-

Specialization allows reps to be more efficient. For example, if you keep one sales rep for prospecting and one for closing, they become experts in their field. If your margins support specialization, do it.

Hire strategically. You should not be spending time training reps on how to sell. You want to be training them on your product. When you begin hiring more than 2 reps per month, hire them in groups and invest in training classes. Over invest in the beginning, because it will pay huge dividends later on.

Make culture a priority, and include that in training as well.

Org structure and promoting-

Each closing rep manager should have 8-10 direct reports. SDR managers can handle a bit more. Be sure to keep the org chart simple. Additionally, promote from within if it is the best option, but don’t force it.

Be careful not to set unrealistic expectations around promoting. We started a trend where we were promoting people after 3 months, then as we grew and hired more salespeople, they were expecting to be promoted after 3 months when the positions weren’t available. Be sure to communicate and set realistic expectations in the beginning.

7 Deadly Sins That Startups Make & How To Avoid Them

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled 7 Deadly Sins That Startups Make & How To Avoid Them, by Gabu Luna-Ostaseski.

There is this myth in Silicon Valley that some people have it all figured out and have all the secret sauce for creating great companies. The truth is that growing my business has been the hardest thing that I’ve ever done. I went through some dark times growing my business, and lot of the challenges happened between achieving customer validation and getting ready to scale.

Startups have a predictable growth cycle:

  1. Customer Discovery – you’re trying to put out a minimum viable product (MVP) and trying to put some product out there.
  2. Customer Validation – as you begin to accelerate as a business, you’re focused on hitting customer validation. This usually happens after 3 to 6 months.
  3. Upshift – this is piece that most businesses don’t talk about and where I think most businesses fail. This is where you’re focused on developing a repeatable process and getting ready to scale.
  4. Scaling – this is where you start to grow and stabilize. Initiate your repeatable process and grow.

The Upshift phase is uniquely challenging phase in the growth of your startup. Today I’m going to focus on 7 deadly sins startups make and how to avoid them.

7 Deadly Sins During the UpShift Phase

Sin 1: Boiling the Ocean – You cannot boil the ocean. In other words, you cannot break into all markets, segments, and industries at the same time.

When my business first got started, we were in 14 different markets and 7 verticals. What we found out though was that our best customers were coming from just 2 categories. Once we found this out, we made the tough decision to scale back and focus on these two categories. As a result, we were able to double the size of our business.

How to Avoid:

  • Focus on less segments & verticals, optimize them and then replicate them
  • Focus on customers with the most urgent, pervasive, and costly need.

Sin 2: Hire an Architect, Not a Builder – I believe it was Jason Lemkin who said, “Hire your first VP of Sales so that you can fire him/her, and hire your second VP of Sales.” It’s very rare for someone to be able to both architect a plan and initiate it as well. I hired 3 VP of Sales before I found someone who was a good fit for the role. Finding someone who is an architect and a builder is like trying to find a unicorn.

How to Avoid:

  • Recognize these are two different jobs
  • Blueprints first, build second

Sin 3: Scaling Prematurely – My business tried to scale prematurely at $8 million ARR and I almost bankrupted my company. I hired 40+ salespeople and we began doubling the number of deals each month and it seemed like things were going well.

A few months into beginning to scale, we noticed that our churn was beginning to rise dramatically. We went from an expected LTV of $5000 to $800 in a series of a few months.

In other words, we had not built a scalable, repeatable business yet. I had to fire 35 salespeople as a result in order to keep the business alive.

How to Avoid:

  • Recognize the difference between traction and scale
  • Get salespeople profitable before hiring more.
  • Total visibility into all stages of the sales process.

Sin 4: Burning Cash – Are you a startup with a ping pong table? Do you really need that ping pong table to get more revenue?

One big issue that startups have is that they spend money on things that don’t get your revenue. You need to make sure that you’re putting money towards things that lead to profit if you’re growing your business. Buying a ping pong table isn’t going to destroy your business, but it’s money that could be spent towards something that is going to directly impact your bottomline.

How to Avoid:

  • Start charging early
  • Focus on getting to breakeven
  • Cut frivolous spending

Sin 5: The All in One Salesperson – One common issue at startups is that their salespeople spend too much time doing things that don’t drive revenue. I encourage startups to focus on figuring out how to make things more efficient, automate, and specialize.

How to Avoid:

  • Segment job roles
  • Delegate or outsource low leverage taks
  • Remove client success from responsibilities

Sin 6: Relying on emotion over data – Most of the time when I ask companies who the most valuable customer profile is, the most powerful person in the room will tell me, “this is who I THINK it is.” Instead of focusing on what you think or believe, focus on what your data is telling. Look at your data and understand what’s most important.

How to Avoid:

  • Remove ego from decision making
  • “What do the numbers say?”
  • Let data drive decisions

Sin 7: Flying Blind – If you don’t know what should be happening at each point in the sales process, you’re not ready to scale. How are you going to grow your company and reach your goals if you’re flying blind? You need to break down your goals and understand what you need to be doing day-by-day, week-by-week, month-by-month at each point in your sales process in order to be successful.

You don’t necessarily need to manage by revenue in – you should also be managing by specific actions that should be completed. For example, think about the # of bookings that each sales rep should be making each week, each month, each quarter, etc. in order to grow your business to your goal.

How to Avoid:

  • What gets measured gets managed
  • Trending in reporting
  • Identify and manage lead measures

From Trials to Triumphs, the Role of Customer Success in SaaS

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled From Trials to Triumphs, the Role of Customer Success in SaaS by Des Traynor, VP of Customer Success at Intercom.

Today we will talk about the role of customer success in trials for SaaS. We have gone from a world of buy before you try, to try before you buy. With this, there has been a shift from committed, guided and experienced onboarding to essentially a warehouse of information. It is dangerous to think that everyone can work everything out themselves.

In the typical SaaS flow, we usually see pre sign-up, sign up, trial start, trial end, then the lead becomes a customer or a failed trial.

At end of the trial there is a decision point. This is where many decide whether or not they see value. It is important to remember that decisions almost never involve money alone. They knew the price when they signed up. We must add intangible value prior to them reaching the decision point.

When breaking down ways that our trials don’t convert, we often struggle. Our products get better over time (we think), and we continue to add features or other capabilities, but if we make our product more complex, it becomes harder it is to focus on core competencies. It is important to make sure these features are adding value to the customer. Don’t become too bloated.

Additionally, as we add value to the product, we must also capture more value. Don’t be afraid of increasing price. With consumers, value is based on perception. However, if there is a gap between the value they expect and the value they get, trials can be lost. Bloat is a non-monetizable feature.

What can we do to make sure we add value in all forms?

1 – Know what success means to your customer:

    1. Ask what your customers want?
    2. Why did they sign up for the trial?

2 – Have targeted help, support, documents, tutorials, and case studies to help them succeed.

    1. Customer success has to focus on what the customer needs to be successful and fit your plan to that. This will ensure the customer is seeing value through the entire life cycle.

3 – You will see signs of a failed trial before it happens. Don’t wait until it fails to take action. Learn to predict and pre-empt a failed trial

  • Regular users use your product regularly
  • Failed users will not have much involvement with your platform, or will seem disengaged
  • Put your trial users in “buckets” of what they are expecting out of the software. From there, you can determine signs of failure specific to those initial goals.

**Example, if the customer signed up for a trial of your marketing product because they wanted to boost conversions, but they are not messaging users, they may need nurturing or education. This is a good chance to reach out to them with 1:1 valuable resources.

It is important to remember that even with these steps, some you will win, some you will lose.

With these steps, when your lead hits the end of their trial they will have much more information to determine if your product is the right one to help them achieve success.

In Summary:

  1. Know what success is for your customers
  2. Ensure your messaging guides them toward their success
  3. Know what failure looks like, and step in to prevent it as soon as possible

Aligning Sales and Customer Success

*Editors Note: Live updates from the Sales Hacker Conference San Francisco are brought to you by PipelineDeals. PipelineDeals is sales and CRM software trusted by thousands of companies to increase sales. Follow us @pipelinedeals.

This session is titled Aligning Sales and Customer Success by Cliff Cate, VP of Customer Success at ToutApp.

An alternative title for my presentation would be Sales + CSM = Happiness & $$$ (CSM = customer success management).

Why should we all care? Everything has changed.

  • Subscription Economy: customers only pay for what they need, they stop paying once there is not good value.
  • Customers are more knowledgeable: 80% of the buying process will happen before any human to human communication.
  • Power of Advocacy: prospects, customers, and former customers are all connected and they like to tweet.

When it comes to revenue, it’s not just about getting new bookings anymore. In the subscription economy, you need to focus on renewals, upsells, and cross-sells in order to be successful.

This means that most of your revenue is going to come after your initial booking. According to most models, only 5% to 30% comes from the initial sale. 70% to 95% of the lifetime value comes after the point of the sale.

For customer success managers, we know that happy customers are more likely to buy than unhappy customers. There is a lot of value and revenue available from happy customers.

12 Tips for How Sales and Customer Success Can Work Together

Before Closing a Deal

1 – Go after the right customers – talk to customer success managers and ask them to identify the most successful customers.

2 – Learn and use customer success stories – drag CSM’s into your sales meetings, have CSM present at your weekly sales meetings

3 – Teach customers best practices – document and teach the three things your best customers do with your product.

4 – Connect prospects with existing customers – always find ways to introduce them to your existing customers. This type of social selling is extremely powerful

Post Close

5 – Quick internal hand-off to CSM – have a checklist of items that need to be completed and move quickly. As a salesperson, have a transfer of knowledge so that you’re not the bottleneck as a salesperson.

6 – Kickoff call with customers – within 48 hours, have clear expectations of next steps and clear points of contact and responsibility.

7 – Initial value check-in – quick email/call to confirm value. Schedule it in advance.

8 – Social advocacy – ask for a recommendation on AppExchange, Twitter, and G2Crowd. You want to ask for a recommendation during the honeymoon period.

Ongoing and Expansion

9 – Health checks – review usage, benchmarks, and best practices.

10 – Get customers together – happy hour, dinners, LinkedIn, etc.

11 – Social Sharing – consistently share content on LinkedIn/Twitter.

12 – Bottoms-up feedback – send surveys to get end user feedback to review with leadership.

5 things to start tomorrow

1 – Buy CSM a coffee/beer and get them to tell you about their favorite customers.

2 – Buy CSM a coffee/beer and brainstorm with them the customers where you think there is the most opportunity for you to grow.

3 – Introduce three prospects to three customers via LinkedIn

4 – Have a CSM present one customer success story at your weekly sales meeting.

5 – Send a survey to the end users of your customers and then review the results with your sponsor. Ask them to rate your service (1 to 5) and list the top three benefits.


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