The opportunity to move into a management role can be a big next step in any salesperson’s career — but it doesn’t come without its challenges.
As Mid-Market Sales Director Christopher Bowman noted, “You could be the best sales representative out there, but if you move into a leadership role and don't understand your people are an integral part of the success of the business, you'll never be successful.”
In talking to sales leaders from six local tech companies, we heard lots of valuable advice, including (over and over again) that many of the skills that make someone a great salesperson don’t translate to a position in management. But career growth is all about stretching yourself and, yes, learning some hard lessons along the way. See how these sales managers turned their challenges into growth opportunities — and how you can, too.
1. Your Team’s Successes (and Failures) Have a Direct Impact on the Business.
Yes, sales can be a grueling career, but it also gives people the unique opportunity to see the very real impact their work can have on the broader business. For managers, this opportunity (and the pressure that comes with it) is magnified.
Director of Corporate Accounts Lindsay McNeese said learning this important lesson has been a tremendous motivator and has served as a guiding principle when coaching her team at Convercent.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
The hardest lesson I learned was also the most valuable, which was the fact that achieving (or missing) our team’s sales goals has a direct impact on the company achieving its overarching business objectives. Someone once told me, “You’re only as valuable as your last quarter and your next quarter.” As a rep, you know this, but often fail to appreciate the “why” behind it.
Understanding this delivers an entirely new outlook on how important you are, and it’s my job as a leader to instill this sense of purpose in each member of my team. This is important in every company, but exponentially so when you’re in a startup or mid-stage organization positioning itself for growth.
It’s my job as a leader to instill [a] sense of purpose in each member of my team.”
What advice do you wish you would have heard before taking on your first sales manager role?
It’s not just about the deals. My priority is in motivating a team, emphatically reinforcing when things are going well and compartmentalizing when things take a downturn. It truly is a constant cycle, and as the captain of the ship, it’s my job to keep the “game” fresh and ever-improving.
2. There’s No One-Size-Fits-All Approach to People Management.
Part of what makes any team great is a diversity of perspectives, thinking styles and learning methods. But according to Mid-Market Sales Director Christopher Bowman, that’s also what makes people management so tricky — there’s no one-size-fits-all approach.
As a sales leader at Denver-based Sumo Logic, Bowman works to tailor his management style to the needs of each individual on his team. For some, that means clear goals and expectations and a detailed plan to achieve them. For others, it means a hands-off approach that gives them room to chart their own path to success. In either case, Bowman said his salespeople — and their continued growth — are his number one priority.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
I think the hardest lesson you learn as a sales manager is that everyone needs to be overseen or managed in a unique way. Some people need and want specific instructions, while others can view that as overbearing and prefer autonomy. The challenge that arises as you adopt this methodology is doing it at scale. Realizing this has helped me better coach people in individualized ways, which enables the team as a whole to thrive.
Some people need and want specific instructions, while others can view that as overbearing.”
What advice do you wish you would have heard before taking on your first sales manager role?
People are crucial, and building a core culture that promotes growth within those people will bring in other good people. You could be the best sales representative out there, but if you move into a leadership role and don't understand your people are an integral part of the success of the business, you'll never be successful.
3. Talk Less. Listen More.
Being a great sales leader doesn’t mean you always have to lead conversations with your team. In fact, according to Partner Development Representative Manager Sophia Kamp, great sales leaders do the opposite — they listen.
By sitting back and letting her team at Xero be heard, Kamp has been able to strengthen the bonds she shares with her sales reps and create a more collaborative and empowered culture.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
Going from a salesperson to a sales manager meant I had to stop doing the talking with my team and do more of the listening. Leadership is not about one voice but rather a collective and collaborative voice where you can give your employees the platform to speak, share ideas, be heard and feel respected and included. Since I’ve learned to start talking less and listening more, I've been able to build deeper relationships with my team and create better processes that everyone feels a part of.
Leadership is not about one voice but rather a collective and collaborative voice.”
What advice do you wish you would have heard before taking on your first sales manager role?
The one piece of advice that I wish I had received, and that I would share with others wanting to get into management, is that you take on both the wins and successes as well as the downfalls and hardships of all your employees. This applies to not only work wins and defeats, but also personal matters because you build relationships with your team and become invested in them. If you have an employee who is struggling, hurting, going through something hard, you take that on and feel wholeheartedly for that individual and whatever they are going through. It is so awesome to be a part of people's wins, successes and growth, but be prepared to take on the hard, sad and intense moments of your employees’ lives and careers as well.
4. “What got you here will not get you there.”
The skills that made you successful as a sales rep are not the same skills that will make you successful as a sales manager, and this can be a tough truth for many leaders to face — even those who have a propensity for leadership.
For Todd Neu, SMB acquisition manager for Zoom Video Communications, the transition to people management required him to embrace a new normal when it came to the structure of his days and to keep the team’s common purpose at the center of everything he does.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
A common expression in sales is “What got you here will not get you there.” I quickly learned this applies in the transition from sales to management. I was used to having a consistent, organized approach to my day, week and month. It helped me succeed. As a manager, though, I have to put the needs of my team members first, and this sometimes seems to distract from the tasks I need to accomplish each day. I'm learning to be mindful of the ultimate goal — growing and learning from team members, helping them get to where we need to be — at the same time I deal with daily challenges.
As a manager, I have to put the needs of my team members first.”
What advice do you wish you would have heard before taking on your first sales manager role?
Take hard conversations head-on: don't tiptoe around problems. Providing feedback can be tough at times, especially when it is in regards to performance. It's easier if we start from a foundation of trust, understanding we share the same goal: growth as an individual and a team. Feedback should always be constructive and aimed at that outcome. Lastly, I try to remember — even on the hard days — that as long as we bring a positive mindset and work-hard attitude to the office, things will fall into place.
5. Let Data Guide Your Decisions.
We have more data at our disposal than ever before, and Director of Sales Development Joe Yesunas recommends every sales manager take full advantage of it. Not only does a data-driven sales culture help drive better decision-making; it also provides transparency around how and why certain decisions are made and greater stability during times of growth and change — something Yesunas’ team at Matillion knows well.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
The hardest lesson I've learned as a sales manager is always to use data as the foundation for decision-making and execute those decisions in a repeatable and consistent manner using a combination of data and sales process. This lesson, which I learned early on in my leadership career, has made me a better manager because the “why” to any decision can always be explained by the data. This helps with team buy-in and adoption of any new change while also maintaining consistency as things undoubtedly evolve.
You are part of something much bigger once you begin to lead others.”
What advice do you wish you would have heard before taking on your first sales manager role?
Don’t always think like you’re still a rep. It's important to maintain that perspective, and factor that into how you act and make decisions, but you are part of something much bigger once you begin to lead others and must always make the greater good your top priority. Also, always try to be aware of how any action — whether it be in a meeting, an email or even a non-work-related conversation — can impact your team or peers.
6. Focus on the Big Picture.
In the day-to-day sales grind, it can be easy to lose sight of the big picture, even as a manager. But according to Sales Manager Jo Chehouri, maintaining a focus on long-term goals — both personal and professional — is crucial for understanding the impact and importance of daily sales activities.
Chehouri said this shift in perspective helps his team at Signpost to be more resilient and motivated and allows him to be a more effective coach.
What’s the hardest lesson you’ve learned as a sales manager, and how has this lesson made you a better manager?
Learn the real “why” behind your reps’ motivations before trying to coach them on what they do every day. When you’re able to tap into long-term motivation, you can help reps more easily see how their daily actions and hitting their short-term, quota-based goals will lead to success with their longer-term goals. That deeper motivation, in turn, helps them push much harder on the close, get through slumps and overcome their own setbacks in a much more sustainable way than any single short-term tactic, line or hook.
Creating an environment of empowerment goes beyond on-the-job learning.”
What advice do you wish you would have heard before taking on your first sales manager role?
If you don’t stop for lunch, your team won’t. And that’s a problem. Creating an environment of empowerment goes beyond on-the-job learning. It’s also laughing, taking time to reset and relax throughout the day and having team outings where everyone can get to know each other on a more personal level. Seemingly tiny stuff like clapping it up for your team’s little wins (and bigger ones like deals) is as valuable as the larger team celebrations. Oh, and say “thank you.” Often.
