An Interview With Mark Roberge: Navigating the Complexities of Hiring Sales Managers and VPs of Sales

Mark Roberge, Sr. Lecturer at HBS; Former CRO of HubSpot; Author of “The Sales Acceleration Formula”

Mark Roberge, author of The Sales Acceleration Formula, is a graduate of the MIT Sloan School of Management. The sales and marketing expert joined the faculty of Harvard Business School three years ago and, in addition to teaching, advises, invests in, and serves on the board of a range of startups and businesses of all sizes. However, Mark’s career foundation was not rooted in sales, but rather in engineering and coding. He credits the innovative ways upon which he approaches sales and marketing strategies with this career foundation of data, science, and process.

In grad school, Mark sat next to a future founder of HubSpot, and shortly thereafter joined the team to run sales when the company was only three people. Seven years later as SVP of Global Sales and Services, Mark had grown the team to over 400 employees spanning roles within sales, services, and operations across three continents and producing over $100 million of annualized revenue.

In this conversation with Mark, we discussed strategies for hiring sales managers, identifying the best candidates to promote into management, and how sales leaders should work with the C-suite.

What are the potential pitfalls of promoting sales management from within?

Promoting a sales manager can be an enormous challenge, especially for founders or CEOs running sales with minimal prior experience in the field. Many leaders in this situation promote their best salesperson to be the first manager, hoping the seller can replicate their success across the rest of the teams.

However, the attributes that make a good salesperson don’t always translate into that of a good manager. Often, successful salespeople are aggressive, extremely diligent about their personal time, and sometimes even a bit selfish and egotistical. These attributes don’t make for a good leader. Sales managers need to do two primary things well: hire and coach. The skills behind these tasks include delivering feedback effectively, developing morale, reading about the true motivations of individuals, understanding learning styles, diagnosing skill deficiencies, etc.

How do you identify the best candidates for promotion?

Hiring the best sales management candidate is a delicate balance. “What you’re looking for in a manager is an individual who can develop team camaraderie as well as have empathy for individuals,” Mark said. “You also want someone who has the ability to coach and teach skills to their team members.”

Mark’s step-by-step playbook for developing sales managers from within:

• Demonstrate proficiency and consistency across the entire sales process: Some salespeople are exceptional in a few areas, but simply middling in others. If those sales people were promoted, they would struggle to coach their team members with deficiencies in the area where they themselves are weak. A promotion candidate needs to be proficient in all parts of the sales process. They do not need to be the best, just proficient. Mark likes to use an advanced skill certification to test this. He also believes they need to demonstrate consistent quota attainment. Consistent attainment is another indicator of proficiency and is necessary to develop credibility with their future team.
• Complete leadership training. Even a candidate with potential needs guidance. It’s critical to train new leaders on delivering feedback, conflict resolution, and other leadership skills. Leverage best practice readings on these topics and then role-play scenarios they will encounter as a sales leader in your company to bridge the theory with practice. A curriculum Mark used many years back is available here and may be useful for topic identification.
• Hire and manage the next recruit. As a final step in the process, have the sales management candidate interview, assess, hire, train, and manage the next sales recruit while at the same time continuing to own their quota. Mark doesn’t recommend the “team lead” role, where sellers manage reps and own a quota for many years. However, this final step in leadership development allows the candidate to put their skills to use in a safe environment where they can receive ample coaching from the sales executives on these tasks. Continuing to own their quota in parallel tests their ability to time manage effectively.

Mark believes it’s important to always be developing from within, nd prefers to hire 75% of sales leaders internally, and 25% or less externally. Why not develop everyone from within? He believes outside hires bring a fresh perspective of best practices from other companies and avoids a scaling risk should your internal candidate pool be low.

How involved should a sales manager be in deals?

According to Mark, frontline sales managers shouldn’t be involved in deals much at all. He regards this as another potential pitfall: since most have done sales before, they’re used to being completely in control of their destinies. That can make a promotion to management a very difficult change.

Mark counseled one of his best sales managers who was just moving into the job, and she told him her most difficult challenge was losing that control. When she was behind quota, she could catch up by making more calls. “She had a hard time letting go, but really bad things can happen when managers get overly involved in the funnel,” Mark said. The urge to get involved can be strong, but an over-involved sales manager can cause a team to lose confidence, become lazy, and reduce the potential scalability of the manager.

To avoid stunting a sales team’s growth and discouraging sales professionals, Mark insists managers should focus on hiring and coaching rather than closing deals and pipeline management. They’ll need to validate opportunity stages with salespeople to make sure the pipeline is accurate, but they should lean on tech as much as possible and focus on developing their team instead. A sales manager can model work for the team, but their primary role should be to coach.

How is hiring a VP of sales different than hiring a sales manager?

A VP of Sales needs an entirely different skill set than that of a sales manager. VPs own a range of strategic elements such as developing and promoting sales managers, designing the salesperson hiring and coaching framework, developing comp plans, etc. They must also focus on how their department aligns with marketing, customer success, product, and the sales team’s participation in the broader company strategy.

The hiring process for this position is especially challenging. It’s easy to assume because an external candidate has been successful elsewhere, that they can immediately repeat that success for a new company. “Frequently, a company will raise a large venture round and give in to pressure to level up their sales leader,” Mark said. “They over-index their qualification criteria on finding the candidate who has been there done that, who is currently leading the team at another big success story company.”

Mark has seen many organizations take this approach and has watched the new sales leader implement the playbook from their last company, hiring the types of sellers, implementing the sales playbook, and deploying the sales compensation plan that worked at their last company. However, the strategies that worked at their last organization are usually not optimal for the new one because of differences in the context. These context variances are often driven by the stage of the business, buyer type, product complexity, category maturity, and geography in which they are selling.

As a result, Mark approaches outside candidates by testing them on their ability to shift context. “I understand how you hired people at your last job. How will you change it for this company and why? How will you change your comp plan for this company and why? How will you adjust the sales process and why?” The right candidate appreciates context variances and the necessary adjustments to their playbook to match the context.

How do you balance internal promotions with a team dynamic?

Promotions can be further complicated when all of the candidates are internal. Mark has frequently encountered companies that consider several employees for promotion, promote only one, and inadvertently drive the other employees to leave. However, by formalizing the sales leadership development process as previously described, companies can avoid this issue.

The leadership development program can extend over a 12 to 18 month period to keep top performers motivated and growing. For example:

• 3-6 months of a candidate demonstrating they can consistently hit their number and pass skill certifications
• 3-4 months of the candidate enrolled in actual leadership training
• 3-4 months of a the candidate making a hire and developing the new rep

“A 12 to 18 month program like this almost manages itself,” Mark said. “And no one’s wondering why someone got promoted first when there’s a clear program in place.” High performers feel like they’re progressing in their careers, and there’s always a pool of talent ready to be promoted when it’s time to scale. Other candidates may self-select out of the hiring process, but are more likely to keep performing instead of feeling unappreciated.”

What can sales organizations do to make the right sales hires and reduce turnover rate?

There’s more than one way to quantify the cost of an unsuccessful promotion, but the wrong fit for leadership can be devastating. The process of hiring a new team, undoing a sales playbook, and reconfiguring comp plans could take a year or more.

Developing a framework and formula for hiring is essential. Mark believes taking a wider view can help mitigate some of these losses. “I think the reason attrition in sales is so high is that sales has a tendency to be very short-term minded,” he said. “If a sales leader walks into a day with a motivational team meeting at 9 AM, a big pitch to a prospect that could save the quarter at noon, and an interview with a new candidate at 3 PM, I feel they often bring their ‘A game’ to the first two meetings and ‘wing’ the interview. However, the upside of finding your next top seller or downside of making a bad hire as a result of the interview are arguably far greater than the outputs of the first two meetings. The more a company can put into place discipline and processes to be operating not in a reactive mode, but in a proactive mode, the more successful they’re going to be.”