I’ve been a sales leader for eight years, and my leadership “journey” started when I told my new manager I did NOT want to be a sales leader.
I was wrapping up a fantastic year as an AE – #1 on the leaderboard globally out of 150+ reps. My friends were promoting to the enterprise team and I wanted to join them. Even my prior manager of 3+ years was leaving leadership to be an IC on the enterprise team.
My new manager told me he wanted to move me into a “pod lead” position to support the growth of his team as a stepping stone into leadership. I told him “no thanks.”
He said, “You’ll need to help a couple of reps ramp, might as well take the title and a pay bump.”
And that was my glorious and reluctant entry into leadership.
Why I Refused My First Sales Leadership Opportunity
Towards the end of the quarter, I was encouraged to interview for a formal Team Lead role. I remember walking around the office asking people I respected for advice – my goal was still to promote to more senior IC roles but I was becoming more open to the leadership path.
The resistance wasn’t about capability. Like many top-performing AEs, I had proven I could execute at the highest level. But leadership felt like a departure from what I knew I was good at: closing deals, managing accounts, and hitting my number.
The enterprise sales path looked straightforward. My peers were making the jump, my former manager had chosen that route, and the compensation was immediately attractive. Leadership, on the other hand, felt like starting over in many ways.
The Two-Factor Framework for Evaluating Career Paths
Career decisions should be evaluated on two critical factors: how you want to spend your time and what you want to be known for.
As I went through the leadership vs. enterprise decision-making process, I ended up focusing on these two areas. This framework helped me move beyond the immediate emotional pull of either path and think systematically about the long-term implications.
Here’s how I broke down both routes:
Enterprise Sales
- Where I’d spend my time: Mostly with customers, including significant travel to customer locations
- Main skills I’d develop: Become an expert in specific industries, personas, and sales process
- The legacy I’d work to achieve: Be known as the rep that closes the biggest, most valuable deals
Sales Leadership
- Where I’d spend my time: Hiring, developing reps, and improving internal processes
- Main skills I’d develop: Recruiting, coaching, and GTM strategy
- The legacy I’d work to achieve: Be known as a leader that helps others achieve career success
After building this breakdown, I gravitated more toward leadership… for the long-term.
When Short-Term Pain Leads to Long-Term Gain
But I really didn’t want to take the next leadership step at my company as a Team Lead.
The Team Lead role at my company was brutal: I’d have to carry a personal quota of a mid-senior rep while managing a team – two full-time jobs for the compensation of one. I’d work more and get paid less in this role than in an enterprise AE role.
My strong short-term preference was taking the AE role, despite the above analysis of time, skills, and legacy. The immediate financial and lifestyle benefits of the enterprise path were compelling. Less stress, more money, and a role I already understood how to excel in.
This tension between short-term preferences and long-term analysis is where most career decisions get stuck. We know what we want to do next quarter or next year, but we struggle to connect those decisions to where we want to be in a decade.
The Question That Changed My Career Trajectory
The question that tilted the scales was, “What do I want to be doing in twenty years?”
I didn’t want to be running demos, planning accounts, and chasing down deals. I did want to lead large sales orgs and shape companies GTM direction.
Knowing where I wanted to be long-term pushed me to do something I didn’t want to do in the short-term. Sometimes, thinking less about “what do I want to do in the next two years” and more about “what do I want to be doing in twenty years” can help us make better short-term decisions.
This twenty-year thinking cut through all the noise of immediate compensation, comfort zones, and peer pressure. It forced me to be honest about what would actually fulfill me over the long haul versus what felt good in the moment.
From 3-Person Team to Multi-Billion Dollar GTM Strategy
Now, 8 years later, I have my dream job. I lead a sales org of ~70. I get to help shape the GTM direction of a multi-billion dollar organization.
But getting to my dream job now required me taking some jobs I did not want along the way. The brutal Team Lead role was a necessary stepping stone. The long hours, dual responsibilities, and below-market compensation were the price of admission to where I wanted to go.
The leadership development that happened during those difficult early roles became the foundation for everything that followed. I learned to hire, coach, and scale teams under pressure. I developed the frameworks and systems that would later help me manage much larger organizations.
Looking back, the reluctance I felt about that first leadership opportunity was natural. But it would have been a mistake to let short-term discomfort override long-term vision. The question isn’t whether a career transition will be uncomfortable – it’s whether that discomfort serves your twenty-year goals.
