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Sales Leader Interview Series – Victor Adefuye & Jessica Wilkeyson

Welcome to the inaugural post of the BuyerSight Sales Leader Interview series! We are excited to kick things off with two noted sales experts: Victor Adefuye and Jessica Wilkeyson from the consultancy Winning by Design. We recently sat down with them to discuss the impact of increasing automation on sales managers. Below are highlights.


VictorVictor is a Partner and Sales Architect at Winning by Design, where he helps companies to develop strategy and scale their B2B sales efforts with the “Sales as a Science” Methodology. He is passionate about helping salespeople to reach their highest potential.

JessicaJessica is a Revenue Operations Consultant to Winning by Design, where she helps companies scale their go-to-market teams through technology implementation, unified customer data strategy and measurement, and cross-functional business process design.

What are the risks of heavy sales automation?

Victor: Errors are a big issue. These large automation platforms allow you to do a lot of things at scale, but they also require multiple steps to get campaigns set up. Mistakes at any of those steps could be damaging. It can be really embarrassing when 1000 emails are sent out with errors. You can actually damage relationships with potential customers.

Also, another thing to consider is that if you spoon-feed your SDRs all of the content that they’re using in their campaigns, they’re never going to develop those skills themselves. I do think that there’s value in helping reps, but I believe the best reps are those who can come up with their own creative ways of articulating value propositions and getting people’s attention and not just relying on sending out the messaging that they’re given.

How should managers think about adding automation intelligently?

Jessica: I see a lot of positives in sales automation. I think a lot of the positives come from the standpoints of workflow automation and the recording of information. However, I do believe more in semi-automation than full automation without human checking. The risk of full automation is that you don’t ever gut check against your human intuitions, whether it’s concerning a piece of data, an opportunity to forecast, or a person you’re coaching across the table.

Also, related to what Victor said, the risk of errors is very high when using heavy automation without heavy data governance. If you have a very tight CRM system that’s being managed without a lot of freedom for reps to change things on their own, then your likelihood of having clean data is higher, and clean data is important. The reliance on rep-reported and rep-recorded data should be lower when it can be automated.

How is automation changing the role of the manager?

Jessica: Previously, it would take a lot of time for me as a manager to go through 12 reps’ pipelines and say, what’s the deal with this, this, this, this? And I would feel like a babysitter. But now, there are easier ways to see some of the issues that my reps have with reporting data accurately or recording information that improves our ability to forecast as a business. It also opens up different kinds of coaching opportunities. Not, “Hey, you didn’t update the close date on ten opportunities,” but “I see that you’re struggling to get this component of qualification criteria on these opportunities.” Previously, as a manager, I may not have had visibility into that, because I was so focused on calculating the conversion rates rep by rep and doing all of that work manually. I see a lot of opportunities with these tools, if governed properly from a data standpoint inside CRM.

Victor: I think, overall, the biggest change is the set of skills shifting from more technical responsibilities like forecasting to more human skills like coaching. And so, it’s possible that, over time, the profile of an ideal sales manager becomes more and more someone who’s a great individual coach. Someone who is talented in the more interpersonal, motivational, and accountability responsibilities that a coach typically has, versus someone who is spending a ton of time putting together reports for the VPs and the CEOs about what’s going on in the pipeline.

What do you think the “sales manager of the future” will do? In 10-20+ years from now, how do you think sales managers’ work will differ from what we do today?

Victor: My vision has always been that the ideal sales manager is going to be a coach more than anything else. Then, as a consequence, the ideal sales manager will adopt a profile that’s maybe more in line with a psychologist than a football coach. Once all the algorithmic, logical, quantitative, analytical pieces of the job are being done by computers that are better than humans, and less prone to error than humans, then how can you use that information to motivate and change behavior on an individual level?

Jessica: Also, I think, going forward, the role of the manager will be to be the voice of a customer from what they’re hearing on the front lines. And I think the role of the manager will be to work with the other managers — the head of product, the head of marketing, the head of customer success — as a horizontal group of leaders to make sure that the priorities of the organization are aligned to help every team succeed. And in that regard, the manager will have to be an advocate for the customer inside the organization with other departments.

Some great insights from these two experts! Stay tuned for more interviews with sales thought leaders coming soon. In the meantime, find more practical tips and food for thought on our blog.

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