This week's guest
Cynthia Handal
Head of Sales and Business Development, StemWave · Top 100 Women in Sales 2025 · 40k+ LinkedIn followers
On building outbound with no playbook, the leader she wasn't, and the women in sales conversation that's long overdue.
I started this interview series because I wanted to talk to people who are actually doing the work. Not the polished conference version of the work. The real version. Building teams from scratch in industries without a playbook. Figuring out leadership the hard way. Saying the things publicly that most people only say in private.
Cynthia Handal was the first person I thought of.
She built outbound from zero across B2B SaaS and medical devices, two completely different worlds with completely different buyers. She broke into tech sales during a pandemic, relocated, reinvented more than once, and built an audience of 40,000 people by just being honest about what she's learning in real time. She's Top 100 Women in Sales 2025, a published author, and one of the few people on LinkedIn who gives genuinely useful advice instead of packaged inspiration.
She also used Claude to clean up her answers and told me about it at the end, which I respect. Same, honestly.
Follow her. You'll learn something. Here's what she had to say.
What transfers: cold call structure, objection handling, follow-up discipline, building rapport through curiosity instead of pitching. The fundamentals don't care what industry you're in.
What doesn't: ICP. Completely different landscape. In SaaS people tell you to move fast and be aggressive. In medical devices, people are polite, super responsive over email, and I would have never guessed LinkedIn would work. We get 1-3 meetings a day from LinkedIn now. At the start I thought it would never work.
Because messaging feels like leadership and infrastructure feels like ops. Messaging is visible. You can see a great email and feel smart. Infrastructure is invisible until it breaks. By then your team is already demoralized.
What breaks first: territories. Everyone calls the same prospects. Reps start competing instead of prospecting. Morale dies. Then cadences collapse, reply rates go to zero, and you buy five tools that don't talk to each other. Reps are manually moving data. Burnout. The pattern I keep seeing: leader hires a VP of Sales. VP says "we need better messaging." Ninety days later reps are still struggling but now they have a new email template. Nobody knows who owns what territory. And somehow the answer is still better messaging.
"Messaging is visible. Infrastructure is invisible until it breaks. By then your team is already demoralized."
I've seen this exact pattern more times than I can count. The territory problem is always the one nobody wants to touch because fixing it means having uncomfortable conversations about ownership, accountability, and the fact that the current setup isn't working. It's easier to rewrite the email template. At least that feels like progress.
Expecting Claude to solve your job and do everything for you. I love Claude, don't get me wrong. It solves the manual part and buys me time. But I still revise every email, every answer. The overcorrecting is still me talking. Claude just fixes my messy grammar.
The line is: are you using it to think faster or to avoid thinking? Those are very different things.
I was micromanaged. That's all I knew. So when I became a leader, I micromanaged because it was my template. I didn't know another way. My managers had controlled everything: how I made calls, when I sent emails, what I said on discovery calls. I internalized it as "this is what leadership looks like." So I did the same thing to my team.
I couldn't delegate without hovering. I didn't trust reps to figure things out. Everyone had to move at my pace. If you were slower, you weren't trying hard enough. I couldn't see that different people need different approaches.
What changed it: therapy. Actual therapy, not just "working harder." Admitting I didn't know how to lead differently. Being willing to be uncomfortable while I learned. And trusting people even when my brain was screaming not to.
The hard truth: I had to stop using my team to process my own need for control. That wasn't their problem. It was mine.
"I had to stop using my team to process my own need for control. That wasn't their problem."
This is something I think about a lot. Most managers who micromanage aren't doing it because they're controlling people. They're doing it because it's the only model of leadership they ever saw up close. You manage the way you were managed until someone or something makes you stop and ask if it's actually working. The fact that she asked that question and then did something about it is the whole thing.
Telling someone what they did wrong without teaching them how to do it differently. That's not coaching. That's commentary.
Most successful women in sales aren't succeeding because of some special sauce. We're succeeding despite burning out from constant calibration. You're expected to be aggressive enough to win but not threatening. Warm enough to build relationships but not soft. Confident but not difficult.
"The real conversation nobody is having: how do we build sales cultures where women don't have to work twice as hard to be seen as half as good?"
Instead, panels keep talking about "leaning in" like the problem is us not trying hard enough. The problem is the system we're trying to succeed in.
This is the most honest thing I've read about women in sales in a long time. Not "here's how to negotiate better." Not "find your seat at the table." The actual thing. The fact that we're succeeding in spite of the system and calling it progress. Panels talk about leaning in like we're not already exhausted from holding the whole thing up.
You don't need to know everything before you start. You need to know enough to start and then learn by doing. Your outsider status is an asset, not a liability. You see things insiders are blind to. Don't apologize for not knowing the "right way" because the right way is often just "the way we've always done it."
Your first ninety days are for getting wins fast, not doing everything perfectly. One win matters more than perfect execution. And people will help you if you're willing to ask. The uncomfortable part is temporary. The regret of not starting isn't.
Listen to your team's calls without telling them first. Not to catch them screwing up. To catch them doing something RIGHT that they don't realize is working. Bring what you find back to the team: "I heard this on a call and it worked, can we all try this?"
Now you're coaching from what's actually converting, not from theory. One Monday morning of actually listening will teach you more about your team's problems than a month of one-on-ones.
I do this. It changes the whole energy of a coaching session when you lead with something someone did right instead of something they did wrong. Reps are so conditioned to call review meaning bad news that when you flip it they don't know what to do with themselves. Then they actually listen.
That growth is not linear.
Growth can be finding a stable job with amazing culture and stability. Not chasing titles. Not climbing the corporate ladder.
I was a CMO at my last company. On paper it looked amazing. But I was so miserable and unhappy. Toxic work environment. The title meant nothing when I dreaded showing up.
"Growth can be finding a stable job with amazing culture. Not chasing titles. Not climbing the corporate ladder."
This is exactly why I started this series. Cynthia didn't give me packaged answers. She gave me real ones. The micromanagement admission. The women in sales take that will make some people uncomfortable. The CMO role she was miserable in. These are the things most people edit out. She didn't.
Go follow her on LinkedIn and visit her website. She's one of the people in this space who actually has something to say and isn't afraid to say it.