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PODCAST 105: Working From Home & 2 Factors to Organization Alignment with Jessica Wilkeyson

This week on the Sales Hacker podcast, we speak with Jessica Wilkeyson, Co-Founder and Principal at Alternate Route, a go-to market strategy and revenue operations consultancy based in New York. She helps growth-oriented B2B, SaaS companies design, implement, and optimize their data strategies, business processes and existing tool stacks to support their customers. Today, Jessica helps companies find ways they can optimize their current business processes.

If you missed episode 104, check it out here: PODCAST 104: Embracing Authenticity to Connect and Drive Revenue with Shari Levitin

What You’ll Learn

  • The importance of sales and marketing alignment reales on communication and measurement
  • Data integrity is more important than you thought
  • Managers working from home need training in empathy and support
  • Reps working from home need to be willing to converse without selling

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Show Agenda and Timestamps

  1. Show Introduction [00:02]
  2. About Jessica Wilkeyson & Alternate Route [1:53]
  3. Sales & Marketing Alignment [3:50]
  4. Data Integrity & Alignment [12:32]
  5. Working From Home as a Manager [22:05]
  6. Working From Home as a Rep [28:48]
  7. Sam’s Corner [36:12]

Show Introduction [00:02]

Sam Jacobs: Hi, everybody. It’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Today I’m excited to have my friend and New York Revenue Collective member Jessica Wilkeyson on the show. She’s the founder of a consulting organization called Alternate Route, which is focused on helping companies align and integrate sales and marketing effectively.

I hope that you are safe and sound. We’re on a global lockdown as far as I can tell and I don’t think that’s going to change by the time you hear this, so I just hope that you’re staying safe. I hope that you’re finding time to take a break. I hope you’re finding some way to demarcate the day and the night, the weekend and the day, because that stuff can drive you crazy.

Now before we get to the interview, we want to thank our sponsors.The first one is a company that everybody’s heard about — DocuSign. Every sales org feels the pressure to close deals faster. Take control with the DocuSign agreement cloud, a suite of tools that automates sales contracts and quotes ,all right in your CRM. Create custom contracts in a click, sign them digitally, and automatically pull data back into your opportunities. See why more than half a million businesses use DocuSign with a free trial and discount exclusively for Sales Hacker listeners at go.docusign.com/saleshacker.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Jessica Wilkeyson.

About Jessica Wilkeyson & Alternate Route [1:53]

Sam Jacobs: Today, on the show, we’ve got a friend of mine and a great consultant in the New York City area. Her name is Jessica Wilkeyson. She’s the founder of Alternate Route, a go-to market strategy and revenue operations consultancy based here in New York. She helps growth-oriented B2B, SaaS companies design, implement, and optimize their data strategies, business processes and existing tool stacks to support their customers. Talk to us about your business and how you started — give us an overview.

Jessica Wilkeyson: About two years ago, I left corporate and I decided that I wanted to focus on helping sales marketing and customer success teams align the way that they work together better. I noticed a lot of siloed behaviors and the companies that I worked at. That was really the basis for wanting to go out on my own. Today, I help companies look for ways that they can optimize and improve their current business processes or create business processes for the first time around an area where they might be really struggling. As a result, especially in a time like this, it could have a critical impact negatively on their business.

Sales & Marketing Alignment [3:50]

Sam Jacobs: What are the indications that sales and marketing and customer success are not aligned? How do we know when that’s not working right?

Jessica Wilkeyson: The first way you know is how frequently those teams are meeting together and working together and sharing insights and learning across the organization. And there’s lots of different ways that you can collaborate and do that. But if there is no process in place for even just sharing what one team knows about a customer with another team, that’s a number one red flag.

The second indicator is the motion that each team goes in. Ideally today especially with revenue organizations becoming more and more integrated, if each team is behaving even slightly differently we’re going to see a lot of inefficiency and a lack of productivity for the whole organization to drive forward. Everyone has to take a mindset of the fact that there is no pride in ownership. Let ideas flow so that the best opportunity to win and serve and help your customers is the one that we put forward.

Sam Jacobs: Let’s talk about your practice at Alternate Route. When you think about the most common business problems that you’re dealing with as a consultant and how you’re helping your clients solve those problems, what are they?

Jessica Wilkeyson: The first one is data. A lot of companies whether it’s HubSpot or Salesforce in terms of the CRM that’s been implemented, it’s been implemented either years ago or without any documentation for how and why things were done. And so most teams really struggle to see their customers and the information that they need about their customers in a single view. A lot of teams don’t trust the data that’s in Salesforce and so they don’t use it to take further actions. So the number one issue I see is data integrity, data accuracy issue with Salesforce and other CRM systems.

The second issue that I see is the implementation of a certain technology, but very, very low adoption. So companies going out, they bought this SaaS platform to help with X, Y, and Z. And then they didn’t really finish implementing it or nobody is using it or nobody is maintaining it. And so lack of enablement through tech is another challenge.

Or the messaging is off. Even recently I saw a number of companies send out messaging given the climate that we’re in today on March 23rd that was not appropriate. And so because these tools are automated in certain cases at 100%, we set and forget them. It impacts brand and perception and the human element of what these engagement platforms at scale are meant to provide. We’re just using them as a way to check a box instead of using them as a way to really personalize and thoughtfully message our customers and engage with them.

Data Integrity & Alignment [12:32]

Sam Jacobs: You mentioned that the biggest challenge is data integrity. What are some steps? How should we think about getting a handle on this difficult issue?

Jessica Wilkeyson: Anything that’s rep reported or required to be rep reported is going to have a huge margin of error in the accuracy and in the timeliness of that data being recorded in your system. So if you as a leader are making all of your decisions only based on what reps are putting down, anecdotally there is so much information missing from the context of just that data that it almost doesn’t make sense if there’s no way to automate the recording of some of that activity back to CRM. So that’s where I do think that engagement platforms and other platforms that write activity history back to CRM become really valuable in terms of measuring the efficacy of your process.

The first thing I would do is look at how much of the data is free text and not required. So you can put certain guardrails in place so that if your accounts and contacts aren’t related, relating those things is a basic step you can take to starting to clean up data integrity. Implementing something like a lean data to route contacts and accounts to leads, to contacts and accounts where a rep might own something faster.

Looking at enrichment tools, provided you’ve mapped out your ICP and you understand where your opportunities are, because you’d want to do that before spending on enrichment. That would be another way to make sure that you’re improving your data integrity. But you can start to make small steps forward requiring different things, rolling out SLAs, not putting it all on the rep but using the automation and sync capabilities of the tools within your stack to help record some of that in a more efficient way are a couple of suggestions.

An easy framework to start implementing things like that would be something like a RACI framework where you have different levels of ownership and different levels of accountability for the roles within a certain team or a cross team function for a process that you want to run or a service that you guys are going to provide to one another. A lot of the skills that you need today to work well together across departments almost look like project management skills.

Sam Jacobs: Yeah, they absolutely do. So data integrity, alignment, one of the other lessons that you’ve learned is you know the importance of investing and marketing and how to think about hiring sales people. So talk to us about your perspective there.

Jessica Wilkeyson: Today, for many organizations, marketing doesn’t generate the lead sales. It’s supposed to generate their own leads and I just don’t agree with that because I think that their role is to help and enable sales to generate leads for sales based on what they know about the accounts. Asking sales to own that entire process end to end with no support from marketing is an easy way to burn your team out. And it goes against the concept of alignment which is working together to help the business succeed.

Working From Home as a Manager [22:05]

Sam Jacobs: What’s your advice to people that find themselves newly working from home and to organizations that find themselves remote?

Jessica Wilkeyson: It’s hard. There’s no way around it. There’s a feeling of being stuck and this feeling of cabin fever. You have to really listen to yourself and if you can’t do something right now, you have to not do it and just go and take care of your mind and yourself first and come back to it later. There’s an understanding across companies right now that not everyone is going to be perfect, and yes we need to push forward. But we need to make sure that we’re doing it in the right way for ourselves.

Sam Jacobs: That’s really hard especially because there’s certain managers out there that are super anxious about having their teams all of a sudden be remote. There’s perhaps a lack of clarity around the roles that they have their people doing and maybe a lack of clarity around expectations. Or lack of trust.

Jessica Wilkeyson: I was going to say lack of training.

Sam Jacobs: Interesting. Tell me more.

Jessica Wilkeyson: There’s a lack of training around poor frontline managers, specifically around how to maybe process and coach against execution and how to trust that your employees are going to do the work that they say that they’re going to do. Also how to empathize with the fact that the work that they are supposed to do today is probably not going to get done at the level that it needs to. And I’m not being negative. It’s just a reality. We have to accept that every company is adjusting their forecasts based on the impact on growth due to COVID.

So instead of clamping down on your reps and making them feel anxious because they already feel that way, why not offer a hand of help and say, “What can I do to enable you? What are your blockers?” If reps are out there hearing that their manager is not behaving as an enabler, then that should be communicated to someone so that they can handle that and help address that through training to the manager and better process management across the team.

Working From Home as a Rep [28:48]

Sam Jacobs: Any ideas for reps out there? What’s your advice to those reps on good strategies for continuing to sell in this environment?

Jessica Wilkeyson: So the number one recommendation I would have is to be aware of your mindset before you start your day or before you start an activity in terms of engaging with customers or prospects. If you’re in a negative mindset and you don’t feel like you can be your best self in a customer facing engagement, then don’t. Go do something else.

If you feel like you are in a positive mindset and you want to help, then I think it’s offering a genuine resource, calling somebody and asking them, “How are you doing? We have some resources. Is there anything that I can do to help you? I’m not calling to sell you anything. I’m simply calling because I know that it’s a tough time for everyone.”

If you’re really not getting anywhere with the outreach, it’s okay to take a break and think about something else like account planning. Think about the moment that we’re in and just start conversations with people. It doesn’t have to be about your product. Your product should always sit behind your messaging and especially in times like this.

Sam’s Corner [36:12]

Sam Jacobs: Hey, folks. Sam’s corner. Great conversation with Jessica Wilkeyson. Talking just about the importance of sales and marketing alignment and organizational alignment. Everybody has to understand their incentive structure, understand the key goals of the business. What your job is as a leader is to make sure that those goals line up as much as possible, and that everybody is incentivized to do something that results in collective success for the organization. When we think about alignment, just remember two things. Communication and measurement are the two factors that drive successful alignment.

What We Learned

  • The importance of sales and marketing alignment reales on communication and measurement
  • Data integrity is more important than you thought
  • Managers working from home need training in empathy and support
  • Reps working from home need to be willing to converse without selling

Don’t miss episode 106 next week!

I hope you enjoyed the show. Before we go, let’s thank our sponsors.The first is DocuSign. Execute contracts and get to revenue faster with DocuSign, used by employees in 90% of the Fortune 500 businesses. Learn more at go.docusign.com/saleshacker. Our second sponsor is Outreach, the leading sales engagement platform

If you want to reach out to me with feedback, you can reach me on LinkedIn. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

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