Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…

[NOTE: Hit the play button above to hear me read this post, followed by a special interview with Jess. She’s amazing and adds some great color to the story. And remember that you can listen to this and every post in the podcast (also available on iTunes and Spotify.]
I challenge you to think up a good outcome in your life that didn’t happen after a failure.
You discovered a new favorite food when your regular order was sold out. A recruiter called just as you realized it was time to quit your dead-end job. You met the person who would be your spouse after a bad breakup.
The universe looks out for you.
This happens so often in my life that I almost smile when a failure happens–as it’s a sign that success is just around the corner.
Such is the story of our latest Fleet business launch. I’m excited to share how we met Jess Shuman and decided to back Revelin, her RevOps consulting business.
Trawling for Talent
It’s January 2024, a time of year when many companies have shiny new budgets and strategic plans. And it’s when they give recruiters the green light to make the hires they hope will turn those plans into reality.
My business partners and I have a recruiting business called Hearty. We call it a “boutique” business because we work with a handful of clients at a time. And it’s just a handful of clients because we C-level partners do the recruiting work–usually for tech-related roles with well-known companies.
Most roles are for software developers, which our CTO, Ross, handles. But today I get a call from my friend, John, the Chief of Staff at a high-growth startup. His company needs to hire its first traditional head of sales, and he’d like me to lead the search.
This big role comes at a crucial time for John’s firm. Due to the compensation involved, it could be a six-figure contract for us. So I’m pretty fired up to get going. We have a productive onboarding meeting, and I’m off to the races.
One of the secret weapons in our recruiting business is our network. I’ve been fortunate to have time in the trenches with fantastic talent across multiple companies. In building my businesses, I’ve always kept an eye out for A-players. There are people I worked with 15 years ago who still have a spot on a list of people I’d like to hire again someday.
So, right out of the gate, I reach out to a few of these folks who I think could be perfect for this role. The first reply comes from Paul. But he’s gearing up to launch a startup, so he’s out on this one. He texts back another idea:
“Jess Shuman might be your person.”
I immediately open a new browser tab and search for Jess on LinkedIn. She recently worked at the same big tech company that acquired my last startup. She began there a few months after we finished our earnout and left.
Paul tells me about how Jess was impacted by a layoff when the company was acquired by a private equity firm–right as she was delivering her first child. Don’t get me started on how awful that deal turned out for everyone involved.
Anywho…I discover some other good friends who worked closely with her and discretely ask for their take. They love her, too. Paul makes the intro, and we set up a time.
Now, as a recruiter, the thing you have to realize about interviewing sales leaders is that, well, they are really good at selling themselves. Duh, I know…What I mean is you have to dig past the surface level to learn what they have personally accomplished.
In this case, I know the insides of her last company. Jess started as a VP of Sales and was later asked to turn around the Revenue Operations function. Also called “RevOps,” this is a relatively new discipline that aims to align sales, marketing, customer success, and finance into a data-based forecasting and decision-making engine. It’s a growing need as software companies must be more careful in making spending decisions at a time when investor money is harder to find.
I also know from first-hand experience that the RevOps function was utterly broken when we worked at this company. I still get nauseous when I think back to countless Friday afternoon sales leadership calls when we all argued about whether such-and-such deal was or was not correctly labeled in the Salesforce reports. Decisions were made on gut instinct and political posturing. Finance, Sales, and Marketing leaders barely spoke with each other. And this was a publicly traded company! No wonder we almost always had to pull a rabbit out of our rears to hit something close to analysts’ quarterly estimates.
So I grill Jess pretty hard on how she sorted out this pile of RevOps spaghetti. With a twinkle in her eye, she walks me through her process of remaking the organization. Within months, it became a predictable, more profitable machine–and her work was critical to the company's strategic acquisition a few months later.
We wrap up our conversation, and I hurriedly type up my notes for our recruiting client. She’s my first introduction to them, and I tell my business partners that we might have found the right person on our first intro.
A few days later, Jess meets with our client….and they decide to pass…
In the recruiting game, you learn quickly that clients say “yes” or “no” to talent for various reasons. I move on to other candidates, but this one stings. She’s so damn good.
“I want to be in the Jess business…”
Jess will continue to occupy rent-free space in my mind over the next few months. She’s on my radar for other clients and friends who need an all-star. One day, I receive a piece of content marketing about how the RevOps role is growing in demand among large SaaS companies. I forward it to Jess, and we strike up a back-and-forth.
During one of my replies, I remember I’m a partner in a services holding company called Fleet. When I’m not recruiting for others’ businesses, I’m looking to back leaders who want to start new companies. And I would love to be in the Jess Shuman business. So, I innocently reply in my next email:
“Maybe a consulting business opportunity??
It could be an interesting career direction if you ever want to brainstorm.
If it’s even 1% temping, we should talk!”
She’s intrigued. My business partner, Ryan, and I meet with her in person. We discuss the growing need for RevOps and how to fulfill it. We meet with some friendly sales leaders about the potential, and they get us even more excited.
Flash forward through a few months of fleshing out our plans, and this week, we’re excited to announce the launch of Revelin.
The market need is clear: Misalignment between customer demand and revenue teams costs companies billions in lost revenue. According to Clari, 75% of enterprise companies missed their annual target last year. Post a low-interest rate world, technology companies are under new pressure to add rigor to their investment decisions and operating models.
But if you run revenue like a strategic business process, you plug the leaks, boost results, and forge a competitive advantage. Some call it Revenue Operations, but Jess likes to call it Revenue Alignment. If this is intriguing, you should meet with her.
Brightsiding is a Winning Strategy
It’s funny. This is the second business launched in our Fleet of companies because another company laid off killer talent. Late last year, we did something similar with A2 Influence, a story I told here. I guess two dots make a trendline.
But it’s a lot more than two dots. I’ve met dozens of successful entrepreneurs who started their businesses after being laid off. While ego-crushing at the time, most say getting fired was the best thing that ever happened to them.
That said, most potential entrepreneurs I speak with back out midway through our discussions. As things get more real, fear of the unknown sets in–along with the ego’s desire to hold onto the existing titles and benefits. Sometimes, significant others are less than supportive. The path is not for everyone.
Entrepreneurs believe in themselves. They get antsy when work is too comfortable. And they often have a supportive life partner who wants to see them go for it.
Just as a drop of rainwater finds its way to the ocean, great people eventually find their way to bigger and better opportunities–but only when they trust the awesomeness and allow the universe to work its magic.
You can be Woo-Woo about it, but you don’t have to be. The simple dynamics of a complex adaptive system like our free marketplace mean many invisible hands are searching for solutions. Killer talent becomes known much quicker in our tightly wired networks, and specialized skills like RevOps are all too rare.
I’m thankful that my network steered Jess into our path and that we’ve created our holding company to support founders like her. But all credit goes to Jess for having the courage to leap. She’s going to crush it.
It takes a lot of mental work, but the next time bad luck strikes you, try framing it as a good thing. New doors open when you keep your mind open. Opportunity calls all the time if you relax into life, shoo away the fear, and listen to what the universe offers next.
How we might work together…
Are you interested in launching your own consulting or service business or need help taking your current services business to the next level? Fleet is our holding company for services, and we’re actively looking to build business partnerships with winning leaders. Let’s talk!
Need guidance with revenue alignment or revenue growth management? We built Revelin to serve organizations through fractional and project-based execution, specializing in GTM alignment, CRM optimization, territory design, annual planning, M&A integration, and building your RevOps function to support growth. Schedule your revenue assessment.
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule a time during my Office Hours to discuss questions, feedback, networking, or any other topic! You can also find me on LinkedIn or email.
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Starter Villian
Speaking of startups…even Bond-like villains have to get their start somewhere.
That’s the very loose premise of John Scalzi’s latest book, Starter Villian. Don’t take the title too seriously. This is a fast-paced, fun fictional romp through a near future of secret societies. The excitement begins when a directionless dude is thrust into an alternative world. It’s a beach read that you can enjoy anywhere, anytime.
Does absolute power corrupt absolutely? You’ll have to read to find out.
Tip of the cap, Scalzi fan!