Before beginning your journey into a sales leadership role, it might be worth asking yourself a very straightforward question: Do you actually want to be a sales manager?
To answer the question honestly, Justin Chow, a regional sales director at legal software company DISCO, says it’s worth figuring out what you enjoy day-in, day-out in your current sales environment. Setting off on a path toward leadership can help you plan what steps you need to take to become a sales leader and, ultimately, if the career move is right for you.
“It’s important for a salesperson to take a step back and really consider what it is that brings them excitement and fulfillment in their jobs,” Chow said. “In a leadership role, a lot of your success comes from the success of your team and others you helped along the way, and seeing others succeed has to be something that brings you joy in your job.”
Since he took the director position, he’s found that it’s “provided a purposeful meaning to my work,” Chow said, and that was in no small part due to a sales environment that prides itself on mentorship and opportunity.
But he’s not the only sales leader in the Austin area who’s wanted to take the sales leadership route and been supported in the process.
In conversations with Chow and two other sales leaders from NinjaRMM and Place, they explained how they moved into their sales leadership roles, what surprised them when they took the job, and what advice they have for burgeoning salespeople.
What they do: NinjaRMM provides cloud-based remote monitoring and endpoint management software to managed service providers and internal IT departments.
Give us a brief idea of your career trajectory at NinjaRMM. Where did you start, when did you get promoted into a leadership role and what did you do to get there?
I joined NinjaRMM as the director of channel sales this year after building a sales career in the security software and finance industries. My path to Ninja was marked by going above and beyond in previous roles that steadily prepared me for more strategic work and team leadership. To get to this point, I consistently displayed my perseverance and commitment to growing the company through repeated success as an account executive, volunteering to build and lead a new team in an unproven area of the business that was experiencing rapid growth, and taking on projects outside of my day-to-day role. These actions showed not only that I was hungry for more opportunity, but that I could succeed when opportunities presented themselves.
What surprised you most about your new leadership role?
As soon as I stepped into this role, I immediately realized that I was surrounded by a group of smart, energized and humble colleagues. When you take on a leadership role, it’s expected that you will help motivate and teach others around you. But this role has shown me that the opportunity to learn comes from every member of the team, from the account executives to the CEO. Our company fosters a culture of curiosity and humility that is deliberately practiced each day by everyone, at all levels.
As a leader, you are influencing or leaving an impact with your colleagues through every interaction you have with them.”
What advice do you have for salespeople looking to move into a leadership role?
As a leader, you are influencing or leaving an impact with your colleagues through every interaction you have with them. From the small side “coffee talk” conversations to the broad audience meetings, there’s always an opportunity to coach, lead and influence. Lead by example — others will look at what you are doing to be successful in order to also uplift themselves.
What they do: DISCO provides a cloud-native, AI-powered legal solution that simplifies e-discovery, legal document review and case management for enterprises, law firms, legal services providers and governments.
Give us a brief idea of your career trajectory at DISCO. Where did you start, when did you get promoted into a leadership role and what did you do to get there?
I joined DISCO as a regional sales executive in 2019. From my first day, DISCO provided me with resources, mentors and the runway to become a top-performing sales rep quickly. I was also able to build strong relationships with the sales leadership team, who not only understood my aspirations of moving into a leadership position myself but also helped me prepare and align my growth and skills development to accomplish that goal earlier this year.
DISCO provides an incredible support network for its sales professionals, which enabled me to mentor sales representatives who were a part of my organization. I embraced the opportunity to help my teammates grow in their roles and win deals — I wanted to be available to help them close a deal and bring it home. In fact, I was able to help collaborate on a deal with every single person in my region!
Now in my leadership role, I wake up every day with a shot of energy. From the exciting unpredictability of what each day may bring to helping my teammates grow, it has really changed a lot of my outlook for how I operate day to day. The new role didn’t give me a renewed purpose, but it has provided a purposeful meaning to my work.
What surprised you most about your new leadership role?
Moving into a leadership role as opposed to being an individual contributor requires a lot more time devoted to being reactive as opposed to proactive. In addition to managing my own schedule, I am also focused on supporting my team of high-performing sales representatives. Part of my job is addressing their needs and challenges, developing account growth strategies and providing the support they need to close their deals.
The leadership function also requires more internal meetings and debriefs worked in with client-facing meetings. This is very exciting to me — every single day, I see how I am a part of something larger in terms of DISCO growth and sales strategies.
Know where your strengths and interests are, and pick that path for your career growth and fulfillment.”
What advice do you have for salespeople looking to move into a leadership role?
When considering what career progression path makes the most sense, it’s important for a salesperson to take a step back and really consider what it is that brings them excitement and fulfillment in their jobs. For some, it might be winning that big client or closing a deal you’ve been chasing for two years. For others, the excitement may come more from mentoring new sales reps or helping team members learn and grow.
In a leadership role, a lot of your success comes from the success of your team and others you helped along the way, and seeing others succeed has to be something that brings you joy in your job. Sales can be very competitive, and there are people who thrive more in a me-first kind of role than a team-first role — which is perfectly fine! Know where your strengths and interests are, and pick that path for your career growth and fulfillment.
What they do: Place builds financial forecasting and corporate performance management software for technology and service companies
Give us a brief idea of your career trajectory at Place. Where did you start, when did you get promoted into a leadership role and what did you do to get there?
I joined Place as the first member of our sales team. I was brought in as an AE, but as a one-person sales team, I had a hand in the higher-level strategy as well. In practice, this meant defining our ideal customer profile (ICP) and honing our message for that audience. All the while, I was pounding the phones and setting up meetings with potential customers.
Early on, I identified networking events as a great way to enhance my learning and development. Don’t be afraid to lean on your network or create a network. In a tech hub like Austin, these events are easy to find and a great source to learn the best practices.
As the company grew, we hired several AEs and our first BDR. Coaching these new hires really expedited my professional development. To train new hires effectively, you have to be extremely clear on the objectives they need to hit to be successful and provide effective strategies to get there. Like any great coach, you also have to identify people’s strengths and let them play to them, while simultaneously helping them develop where they need improvement.
After a few quarters as a “player-coach,” I made the official transition to sales manager.
Make your ambitions known to your manager.”
What surprised you most about your new leadership role?
I think the biggest change that occurs when you transition from an IC to leadership is that you have a team of people looking to you for the answers. As an AE, you’re responsible for managing your book of business as you see fit, but you have a manager coaching you along the way. If you ever get stuck, you can turn to them for the solution.
As the head of a department, you’re not relying on someone else to make an executive decision for your team — you have to make the calls and own the results.
During a leadership team meeting a few months ago, I fielded some tough questions from other department heads about a couple of important — but complex — deals my team was working on. With senior leadership stress-testing our strategy to close these deals (as a good leadership team should), I found myself thinking, “Someone should just tell me what to do, and I’ll do it.”
Upon reflection, I realized that I needed to embrace my position and trust myself to make the right calls. Rather than looking for someone else to give me the answer, I needed to gather all the facts, lean on my teammates for insight, then come up with a strategy, execute and take ownership of the results.
What advice do you have for salespeople looking to move into a leadership role?
Identify people who are excelling in their leadership roles. Take note of what they do differently than the average performer and embrace those traits. Don’t be afraid to reach out, be bold and leave your ego at the door. Take the opportunity to just learn more about their journey. Just be sure you have a game plan going into the conversation. One question I always like to ask is, “What would you do differently if you knew what you know now back when you first started?”
Make your ambitions known to your manager. If they know what your goals are, a good manager will give you the honest feedback you need to get where you want to go. That said, it’s a two-way street — if your manager regularly gives you advice that you consistently don’t implement, they might start to question how committed you are to your stated ambitions.
This last one can be tough for ambitious salespeople: Don’t burn the candle at both ends! It can be tempting to log late-night hours prospecting then clock in early the next morning to get a jump on meeting prep. While pushing yourself is important, you’ll burn yourself out if you overdo it. And once you become a manager, your team will follow your lead!
