All I could see was the failure
READ TIME: 4 MINUTES
Clients tell me the story they don't tell hiring managers.
The losses. The tough times, some driven by the company, some by their own choices. Some joke that I'm their therapist.
I also hear the wins: the President’s Club trip, the $500K deal, the quarter they closed more deals than anyone on the team.
Even with those wins, many are weighed down by the losses. They don’t know how to talk about a missed quota, a layoff, or leaving a company after 9 months.
Why it's hard to see your own story
When you're too close to it, you can't articulate the value you bring. You see the loss and skip the win.
That's a problem, because hiring is speed dating. Hiring managers get a short window to figure you out. If you don't know your story and can't own it, they won't figure it out for you.
It gets harder with more years of experience. Especially if your path wasn't linear, or you've covered a wide range of roles and responsibilities.
My version
In 2023, I was running my first search as a VP of Sales, and I was coming off a hard stint. I was questioning whether I was good at the job.
I was the VP of Sales at Anvyl, a small startup with 6 AEs, 5 SDRs, a manager over each, RevOps, and a sales enablement leader I hired. When I joined, the goal was to help the existing AEs perform, then scale with more headcount. I'd consulted for them first, so I had good insight going in.
What I missed: it wasn't just a sales skills problem. It was a pipeline problem driven by a product-market fit problem.
Not enough marketing leads and inbound volume. No clean ICP lists to target. Messaging that didn't resonate. A product that struggled in specific verticals, and a competitor that was performing.
On paper, the opportunity was there. But it needed product changes, marketing changes, and the right foundation for the sales team to win.
Without that foundation, we missed our number.
I built the business case to overhaul the product, set the marketing foundation, and scale the sales team down to 1 AE. That meant the whole sales leadership team, me included, was cut.
Before that, I made mistakes. I hired reps I later had to lay off. I should have tested smaller or reset the growth goals. But when the board and your CEO are pressing on the number, those calls get hard.
When it came time to run my search, I sat down to write my story.
VP of Sales candidates tell growth stories: $2M to $5M, $5M to $10M, $10M to $50M. I didn't have one. I had missed the number. From the inside, all I could see was the failure. I was so focused on the outcome.
What got me unstuck
I called Rachel. She ran a recruiting organization and did some career coaching. I'd known her for years and always respected how she ran her business and the values she brought to her team.
I needed an outsider's view. After talking to hundreds of candidates, she could help me break my story apart and see the successes.
She reminded me that most startups fail. Few end in a profitable acquisition or IPO. My story looked like a lot of other heads of sales.
Rachel also helped me own my wins. I was the one who drove the ICP work to focus on our highest-performing segments, which increased win rates. I was the one who secured buy-in from Product and Marketing for the overhaul and presented it to the board.
That's the work you can't do alone. Not because you lack the skill, but because you're too close and too hard on yourself.
What changed in my search
I owned what I learned, and I applied it. The biggest shift was how I vetted companies. I checked 4 things:
Inbound marketing pipeline. Anvyl’s problem started here.
Product-market fit. A product that struggles in its target verticals can't be fixed by sales alone.
Customer count. How many customers do they have?
Retention rates. Are customers staying?
That filter gave me 2 paths: an earlier-stage VP of Sales seat with PMF and inbound already in place, or a larger, established company where I'd be #2 to a VP or CRO leading a team of managers.
I took the second path.
Run your own story audit
For each of your last 3 roles, write down:
What you owned and the results you drove
What broke, and whether it was the system, the strategy, or you
What you'd do differently, and how it changes what you look for next
Then hand it to someone outside the situation and ask: "What do you see that I don't?"
Pick someone who knows sales: a former manager, a peer, or a coach.
Here's the truth: your hardest role isn't a failure. It's a chapter, not the book.
Hit reply and tell me: what's the one part of your story you still struggle to own? I read every response.
To clarity and confidence in your career path,
Amanda
See you next Sunday.
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