4 Reasons Why Founders & CEOs Can’t Step Away from Sales: My Coffees with Doug Wilber

by Amy Kohl

In the highly competitive B2B SaaS industry, building trust and relationships with customers is crucial for success. CEOs and founders often find it difficult to step away from sales due to the importance of fostering genuine connections with clients and establishing a foothold in the industries in which they serve.

I often meet former client and friend of mine Doug Wilber, CEO of Denim Social, for coffee and happy hour. He’s always been an excellent sales-oriented leader and, although never labeled with a “sales” title, has extensive practice building and rebuilding sales teams and strategies. He has been an invaluable sounding board for me as I’ve navigated the growing pains of my own business, although at one point he was one of my wildest clients :) 

Amy Kohl and Doug WilberDoug and I during one of our coffees.

A theme that has emerged from our get-togethers is the connection growth-mode CEOs must keep with sales. This post shares the challenges that CEOs and founders find with the conceptual expectations of stepping away from sales and how adopting a philosophical sales approach can help bridge the gap.

1. CEOs listen to listen, which is why customer relationships thrive.

CEOs and founders are simply conversing with people when they’re in selling conversations - they listen and don't pitch. This is why it's so hard to replicate a founder closer.  

In a world where people buy from people, it's essential to build relationships beyond product features and functionality. This means slowing down the sales process to truly understand the customer's needs and offer tailored solutions to their problems.

Demand generation is necessary, but it's not enough to send a few emails and schedule out LinkedIn posts. Follow-up emails must always provide value (APV) - and not self-serving value.  Sales reps should be equipped with relevant content, including press releases, third-party content, and industry insights, to help establish their expertise and, most importantly, serve the prospects. 

Doug shared with me that after analyzing numerous call recordings, it became apparent that his business’s successful sales outcomes were tied to the genuine relationship with the customer. This involved listening to their concerns, empathizing with their pain points, and offering valuable insights. This doesn’t mean small talk about the weather, which is typically just noise and meaningless conversation that robs time from developing a meaningful partnership. 

Doug also recommended analyzing what things led to positive outcomes in the long run. When did they feel comfortable sharing their pain? And not discovery call pain — the real pain behind it. This is the moment the full sales relationship is formed, making you a confidant and partner to finding a solution. 

CEOs and founders often excel in these areas because they are deeply connected to the industry first and the product second. However, replicating this level of expertise and empathy in the sales team can be challenging. We onboard our up-and-comers with extensive product knowledge and expect a deep understanding of the functionality and application of the solution.  But far too often, even the greatest tactical skills will be overlooked without the interpersonal rapport and stronghold on the industry knowledge. This leads us to #2…

2. Industry knowledge from leadership exposure is crucial – WFH is hurting the development of up-and-comers.

For sales teams to succeed, they must commit to learning the industry as much as learning the product. CEOs and founders need to lead by example and teach their teams non-stop. Companies that skip this crucial step are bound to fail.

Unfortunately, the shift to remote work has hindered the development of new teammates, especially the sales teams. Learning opportunities are limited when new employees are on-boarded remotely. Evidence is in the increase in underperformance status of employees and a decrease in role advancement.

In contrast, the original teams that were onboarded in-person continue to operate more efficiently and have absorbed an abundance of experience from exposure to their peers and leaders. This is a massive advantage for pre-COVID employees who are maintaining their performance or achieving high-performance status due to acquired knowledge and self-discipline of the current WFH. 

A tactic that less experienced salespeople employ to compensate for this is posturing through someone else’s experience. “We see this all the time” and “our leadership just shared…” — the use of “we” builds the credibility of the up-and-comer through the power of the council behind them. However, this is hard and most people cannot do it when they’re detached from the leaders from whom this experience stems.

To overcome this challenge, CEOs and founders need to be more hands-on in the learning process and experience sharing. Joining calls, participating in webinars, and creating opportunities for learning can help bridge the gap. However, the sales team, especially low-performing reps, must recommit month-over-month to the industry they serve, and leaders may need to sacrifice some of their own freedom for the betterment of the company and longevity of their up-and-comers. We’ve both had many personal experiences of pushing reps to take ownership of their careers and knowledge of the industry their serving – once they commit to their own growth they absorb and collaborate within the business in all new heights.

After all, professional athletes don't train remotely and get together on game day. Leaders and sales execs shouldn’t be any different—leadership is obligated to teach and sales execs are obligated to learn – but they must “show up” for one another. 

3. Pressure... Just all the pressure. 

There’s no denying the immense ownership felt by those at the top. Pressure to deliver for the Investors. Pressure to deliver for the Board. Pressure to deliver for the employees. Pressure to deliver for the employee’s families. Pressure to deliver for external perceptions of the company. Pressure to deliver for your family. And sometimes most excruciating – pressure to deliver for yourself. 

Doug and I frequently comment that a CEO/founder of a growth-mode company is the worst backseat driver. When your neck is on the line for everything (internally and externally), you must have your hand on the wheel and a foot on the pedal at all times. Not some of the time – all the time. 

You’re always on – even when you’re on vacation, disconnected, and covered in sand building a drip castle on the beach with your 6-year daughter, there’s guilt about the separation between you and your computer. Even knowing you deserve the time off and knowing your team wants to see you take a break too, you never mentally check out because the pressure is always on. 

Far too often, Doug and I have seen other CEOs/founders hand over sales and get burned. If they’re lucky, it happens quickly, but sometimes the realization is delayed far too long –  and the work required to make up for the setback is 5x more than if they had never let sales go.

While hiring trustworthy teammates and fully committed to empowering them to thrive in their roles and with their team, the pressure will never subside enough to allow the disconnect from sales. Good founders are okay with this and learn how to cope with the pressure.

4. Multi-department influence - a reason to grow the leadership team slowly.

The 100-foot view of a customer’s experience not only sets better expectations in the sales process but also brings continuity internally from the top funnel to closing the customer. 

Once the founder hires their initial sales team, they often revert their attention to customer success or another part of the business that requires development. And for good reason – they’ve established a sales process and have backfilled a closer to allow them to dive into another part of the business to keep the momentum going.

After witnessing it and living it ourselves, Doug and I know it is very, very difficult to cross-function a sales leader or customer success leader to drive the continuity and alignment the CEO/founder will. Why? The KPIs that support the role and department drives motivation to advocate differently – solving this with bleeding metrics that cross into the next department have certainly exacerbated this. 

That’s why Doug and I recommend slowly growing the leadership team. Prioritize one department head at a time. The CEO and new leader will work together to uphold the mission and values of the company while setting goals and constant alignment and realignment discussions. Then once a third is added, the leadership culture is at risk of a shift again. The same expectations are in place of goal setting and consistent opportunities for alignment and realignment must take place.  

The direction of the CEO/founder’s focus greatly depends on the alignment of the leadership team, yet it rarely ever leaves sales. Even with a great head of sales in place with a strong process and team, the best companies have a highly sales-oriented CEO. This allows for stronger innovation for the product, tighter sales processes, and stronger onboarding for customer success.

Follow Doug Wilber on LinkedIn – he not only will blow up your feed with posts and videos sharing his candid POV, but he’s also a very collaborative networker! 

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