Building a Sales Engine (And Feeling Like an Awkward Turtle)

My Journey from Founder-Led Sales to “Official” Sales-Led Sales

The stakes? Oh, they’re big. I’m not just here to build a sales engine; I’m here to shift the planet’s consciousness. I’ve always believed a career should be more than just a paycheck. It can be a canvas for self-expression, a vehicle that channels our deepest passions and aligns with our highest visions. By 2030, I’m determined to help a million people discover careers that don’t just spark their interests but elevate their potential to make a meaningful impact on the world.

And let me tell you—this growth journey isn’t all smooth sailing. Sometimes, I feel like an awkward turtle trying to figure out which way is up, bumping into things, flailing around, but still moving forward.

The Familiar vs. the Unknown I’ve built a mountain of processes and have the tech stack experience to prove it. Automation tools, CRM integrations, you name it—I thought I had it all down. But now, I’m stepping into uncharted territory with tools like Clay and Teamfluence. Sure, I’m comfortable learning, but there’s a definite learning curve. And let’s not even talk about LinkedIn Ads. Suddenly, I’m knee-deep in questions like, What makes a good LinkedIn ad? Which campaign solves my unique constraints? It’s both exhilarating and humbling to realize just how much there still is to learn.

Then there’s my pivot from B2C sales, where I’m used to closing with individuals or small groups, to the intricate world of B2B. Now, it’s formal sales processes, buying committees, even InfoSec questionnaires. And let me tell you, navigating the unwritten rules of “sales decorum” in B2B feels like learning a dance I’ve only ever watched from the sidelines. I’m used to hyping people up and cheering them on. Now, I’m the one guiding them through the whole journey and asking for their business. After years of coaching others on GTM, it’s time for me to really walk my own talk.

The Awkward Turtle Moment Anyone who’s navigated a sales call knows this moment: you’re pivoting from educating to closing, and you feel that urge to blurt out, “SO DO YOU WANT TO BUY?” For me, it usually hits during that second call, right at that awkward transition point. It’s where “let me help you” morphs into “let me be the solution you’re looking for.” And yeah, it’s still a bit messy. I’m figuring out how to bridge that gap without feeling like I’m trying to drag them through the door.

The System (And the Bumps Along the Way) I’ve hit a groove with a system that starts on LinkedIn—friendly invites, DMs, and exclusive event invites that spark genuine conversations. Through these connections, potential projects start to emerge. But, of course, it’s not all smooth sailing. Just last week, we had a calendar mishap with our guest of honor, and we only noticed hours before the event. Yikes. But hey, these bumps are part of the process, too.

The win here? I’m seeing firsthand how conversations with the right people can open doors. It’s organic, and it feels true to who I am. That’s the traction I want as I keep building out this sales engine, with the dream of eventually handing it off to someone else.

The Tempting Side Quests and the Stakes I’m Facing Here’s the thing: sometimes, the pull of RevOps work is strong. There’s a thrill in debugging a technical issue or solving a formula—it’s like a little dopamine rush. But now, I have more to lose, and it’s not just about me anymore. I’ve got a team relying on me, people who believe in this vision and trust me to lead us somewhere meaningful. The stakes feel bigger, and I’m learning the true value of their trust.

I think back to my early days in Manhattan, when I was a kindergarten teacher turned waitress, living in 83 square feet and hustling through each day. I’ve been a survivor, thriving on risk. But now? I’ve got a responsibility I’ve never had before, and I’m seeing leadership in a whole new light.

Building in Public – Letting the Guard Down There’s something special about sharing this journey with all of you, warts and all. Building in public isn’t about showing off; it’s about inviting people into the messy middle. It’s sharing my mistakes, insecurities, and little victories so anyone tuning in can feel a little more permission to be themselves. When I share the awkward moments and challenges, it’s an invitation for others to embrace their own growth, too.

Takeaways for Fellow Builders If you’re in the trenches like I am, here are a few things I’m learning:

1. Be Real with Your Team – I’ve been open with mine, and instead of judgment, they’ve mirrored back excitement about building something new. They even ask how they can lighten my load! Honesty fosters loyalty and camaraderie in ways I never imagined.
2. Challenge Unrealistic Expectations – I’ve learned that some of my frustration comes from expecting instant success in areas I’m still mastering. That’s a fast track to burnout! Give yourself the grace to learn, and don’t expect perfection on day one.
3. Get Help When You Need It – Just last week, I brought in a LinkedIn Ads consultant and asked an advisor for help with executive alignment. And now, I’m headed to Austin for the Pavilion GTM 2024 conference, ready to soak up every drop of knowledge I can.

Jacki Leahy is the founder of Activate the Magic , a Fractional RevOps service for early-stage B2B SaaS companies. With a passion for scaling businesses and shifting mindsets, Jacki believes a career should be more than just a paycheck—it’s a medium for self-expression and personal growth.