Guest author: Jaime Konzelman
I used to believe that the path to success in sales leadership was linear, predictable, and, most of all, rule-bound.
Follow the process. Smash your quota. If it’s not about moving a deal forward, there is no space for it in business.
And if you're a woman in B2B sales?
Smile, stay agreeable, and don’t dare be “too much,” of anything.
For years, I played that game and I was good at it. As an enterprise seller , I exceeded my quota every year. In less than five years, that quota increased from $1 million a year to $350 million a year before moving into leadership, leading an elite team responsible for $4 billion a year in new business – overachievement worked as a career growth strategy. I got promoted, climbed the ladder, led teams, and delivered revenue.
From the outside, I looked like the model sales leader. On the inside, though, I was slowly disappearing.
I wasn’t leading, I was shape-shifting. What was worse? I was the shell of the person I once knew whose passion for life outside of deal contribution was all but nonexistent. I was showing up as the version of me I thought the role demanded, not the whole- human leader I was.
That shift, the decision to stop fitting in and start showing up and giving myself permission to bring all of me to all that I do, is where this story really begins.
The Wake-Up Call
I remember the moment it hit me. I was leading a high-stakes sales meeting, presenting the “right” strategy in the “right” tone to the “right” room. But I walked out feeling hollow.
I wasn’t tired from work. I was tired of contorting myself to fit in while abandoning the parts of me that, well, made me the most me.
I realized I was winning in a system that never truly made space for someone like me – a deeply feeling, empathetic human whose passions outside of deals included things like animal rescue, coaching, and even triathlon.
That realization wasn’t discouraging, it was freeing.
Because leadership isn’t about fitting in rather about standing firm in who you are and leading from your own personal power which requires all of you to fully show up in your own unique way.
The Unlearning Phase
What followed was a season of unlearning.
I questioned everything: how I spoke, how I led, the kinds of coaching and training exercises I brought to the table, how I made decisions.
Was this me or just what I was told leadership should look like?
I got honest about the masks I’d been wearing to protect myself in rooms that didn’t always feel safe.
And I got real about the cost, burnout, disengagement, and a kind of quiet resignation that so many women in leadership silently carry.
Breaking the rules, for me, wasn’t about being defiant.
It was about being whole.
When I published my first memoir, Dealmaker – the story of my journey through the world of adult entertainment, I was convinced it would ruin my business career. Yet, I felt called to walk through those doors to be in alignment with personal belief that there is no shame in walking a different path as long as you are being true to yourself.
Publishing my story taught me that my belief in myself had to outgrow my fear of not fitting in and while I didn’t realize it at that time, simultaneously, I stopped seeking approval and started leading from a place of deep personal alignment – and that’s where the magic happens.
I gave myself permission to say the hard thing in rooms that didn’t want to hear it, to question the playbook, and to bring humanity back into how I led revenue teams.
I stopped trying to lead like a man and started leading like a boss. On my terms.
This Isn’t Just My Story
I wish I could say this story is unique. But it’s not.
Across boardrooms and Zoom calls, too many women are rewarded for muting themselves and punished for being powerful.
We’re still teaching leadership like it’s 1985; compliance over clarity, performance over presence, pretending over truth.
That’s why I now live and lead by what I call the No-Mask Model of Leadership.
No contortion. No code-switching. No compromising who you are to do what you’re here to do.
When you show up whole, people stop showing up half.
The Transformation
I’m still a high performer. I still run a cross functional commercial organization. But I lead differently now.
I value presence over posturing. Connection over control. People over politics.
The results have never been better. Teams perform when they feel seen. Culture thrives when there’s room for truth. And the women around me are stepping up, not by emulating me, but by becoming more of themselves.
Because when you show up whole, others stop showing up half.
What I’d Tell My Younger Self
If I could go back and mentor the earlier version of me, the one playing by every rule, I’d tell her this:
You’re not too much. You were just in the wrong room.
You can drive revenue without losing your soul.
Real power is earned the moment you stop performing.
And I’d remind her that bravery doesn’t always look like a stage and a spotlight.
Sometimes it’s walking into a meeting and telling your truth.
Passing It Forward
Today, I coach and mentor rising women leaders who are done playing small. I share my story, not because it’s perfect, but because it’s real.
Because too many women are succeeding in systems that are silently eroding their confidence.
Leadership doesn’t have to be a performance, and you don’t need to earn your seat by erasing your edge.
You can be bold, human, and wildly effective.
You don’t have to choose between ambition and authenticity.
The old rules were written without you in mind. Rewrite them.
