June 24, 2026 / 6 min read

TGC 002 | The One Who's Killing The Sales Game (But Overthinking LinkedIn)

Our first That Good guest is a powerhouse sales expert who spent years closing deals in her career, and now she’s building a business with a sharp premise: most CEOs and founders hire their first salesperson way too early out of the gates, even before they have a system worth handing over. She fixes that by helping clients build out the sales strategy first, so that a new hire actually has a legitimate playbook to run, and not one to invent from scratch.

She coaches founders on her own custom-designed foundational pillars that she has built from her expertise that determine whether a company's sales operation lives or dies. Once, she sat across from one of her CEO clients and, in a single conversation, was able to identity exactly how a certain account executive was embellishing their pipeline declarations. She gave her client three specific, hard-hitting questions to ask to get a handle on things. Case closed.

She knows her stuff, and anyone who's worked with her knows she knows her stuff.

And still: she sometimes spends real mental energy worrying about what her former colleagues might think when they see her LinkedIn posts.

What She Does When She’s at Her Best

In her domain, it all goes back to making sure the foundation is as solid as possible. Before hiring a single salesperson or building the pipeline or writing one word of marketing outreach, her first question to every founder is always: who, exactly, are we selling to? Not simply, who could we sell to? "Who, specifically, is the customer where you would win every single time?"

In her consulting practice, she developed a five-pillar framework for sales foundations built directly from the undeniable expertise that she's gained over years in the industry. When I talked to her, I found myself in awe of how perfectly positioned she is for this and how she could help so many CEOs who find themselves trying haphazardly to land sales when they have countless other tasks to handle. She knows the patterns and she knows what success looks like and she has been on the receiving end of enough failed sales onboarding processes to know exactly where the cracks form - and what to do to prevent them from forming in the first place.

She cuts through the BS.

"There are buyers and there are liars" she shared a line she borrowed from another point in her career, but one she's fully adopted and made her own.

In her practice, she has developed a specific line of questioning for reviewing an account executive's pipeline. "What exactly did they say when you asked X?" She coached a CEO through this exact audit. The $45,000 pipeline evaporated under the right questions.

Most sales folks protect the pipeline at all costs. She interrogates it.

She keeps things professional and stays high when others go low.

When employed at one of those big marketing-software companies everyone in the space knows, she hit record numbers, and then watched management carve her best accounts to give to other reps, raise her quota by 15%, and call that "growth."

She recognized the pattern: the IPO lands, the mission shifts, the culture goes through a glorious period of enshittification. She left for a smaller startup where she was hired to sell to “everyone who would buy,” but unfortunately without a clear objective. She left her next company after a layoff that came a mere 48 hours after a sham PIP (performance improvement plan) - which she actually refused to sign on principle because she knew her metrics were great, and because the friction was personal, not professional.

All of these past experiences have given her this incredible expertise in sales from the ground up, and she has really put herself in such a great position to help founders find their footing when finding their sales targets. I’ve worked with her, and I’m in awe of her “do no harm, take no shit” attitude when it comes to interacting with her teammates, building relationships with customers, and just getting things done.

None of her gritty expertise came from a certification or a methodology course. It came from being in rooms where no one else had figured it out yet, and making moves to actually get the ball rolling.

Field Notes: What This Looks Like in Real Life

Imposter syndrome doesn't care about your track record. She had two decades of corporate sales experience, had already coached CEO clients, had a referral pipeline building quietly through word of mouth, and still felt the "who am I to do this" voice every time she opened LinkedIn and considered posting about her consulting business. The voice isn't evidence of incompetence. It's evidence of visibility and putting yourself out there. The more we show up, the louder it gets, and the stronger we need to be in making the decision to show up anyway.

Sometimes the move is to just to block 'em. When anxiety about former colleagues seeing her marketing posts got loud - the worry about the "who does she think she is" reactions, the cringe and imagined judgment from people she used to work with - she didn't push through it or talk herself out of it. She just blocked them. Gone. No audience, no performance. No problem! It's almost too simple as a solution, which is maybe the point. You don't always have to make peace with the imaginary critics. You can simply remove yourself from their feed.

The financial independence drive is often the origin story. She lost her father at 10 and watched her mother navigate single motherhood alone. She has built up her career as an explicit hedge against dependence - not because she was pessimistic, but because she'd seen what it looked like when women didn't have their own resources. She’s driven to building something of her own, but it isn't ambition for ambition's sake. It's a survival plan formed in childhood and refined over two decades.

Burnout denial is real, and it's a pattern. Sometimes when we feel that we’re burning the candle at both ends, it can insidiously transform itself into a chronic state - not an emergency, one-off occurrence. It can be tempting to write off that familiar approach of burnout as “exhaustion”, as if naming it “burned out” would officially make it Too Much and Too Real. The refusal to admit burnout often keeps high-performing women in situations longer than they should stay.

I remember during a particularly wired and stressed period in my early career, I spoke with my doctor who recommended Xanax. In my head, I certainly couldn’t be at that point because that would mean I wasn’t managing it. (The truth was, I really wasn’t managing it - but I could never let myself accept that.)

The "messy contract" is worth sorting out early. She's currently restructuring terms with a client she described as draining - terms she should have negotiated more carefully at the start. It's a note she made about herself out loud: "I let this slide." The self-awareness to name it and move toward fixing it, rather than grinding through it silently, is its own skill.

We also spoke about being more discerning as we gain maturity with the kinds of clients and work we take on. Whereas earlier in our careers, we’re happy to take whatever it is we can get; now, it feels much better to hold out for the type of hell yes opportunities that we accept with enthusiasm and electricity instead of ignoring that initial this-probably-isn’t-really-for-me instinct.

The Line That Stayed With Me

She said, so simply: "I can go in and immediately identify where the sales process is breaking."

Just like that. No hedge. No "I think" or "usually" or "it depends." She knows she can do it because - well, she's done it, repeatedly, for companies at every stage of growth. That sentence - uttered almost offhandedly, in the midst of the conversation - is the whole point of That Good Club. That's what it sounds like when someone has done the thing enough that the confidence is simply a fact, not just a flex.

What She's Building Now

She's coaching founders and CEOs in the $500K–$10M ARR range who are either struggling to close or preparing to make their first sales hire. She's doing the work she has cultivated over her years in the industry but from an angle that she has more ownership over: sitting with a company founder, diagnosing the exact failure points in their sales motion, and giving them a repeatable framework before they spend money on a hire who won't have what they need to succeed.

Parting words

Next time you find yourself thinking, Who am I to do something like this? Try flipping it and asking instead:

Who am I not to do this?!

And then go do the damn thing.