“Relationships will always separate signal from noise.”
I’ve known Jeff Wald for more than a decade. When I was building a company in the human capital space, he was one of the people I leaned on for advice. So when BoomerangHR announced its $12.7 million seed round on September 14, I wanted to hear the story from him directly. Kalos Ventures and Album Ventures co-led the round, with participation from Monta Vista Capital, Capital Eleven, and Strada Education Foundation.
Jeff spent four years at a venture capital firm before becoming a founder himself. He went on to build Spinback, which he sold to Buddy Media (acquired by Salesforce shortly after for $745M), and then WorkMarket, which he sold to ADP. He founded Boomerang in 2023 and runs it as CEO, alongside co-founders Kanish Raajkumar (CTO), Andrei Tulai (VP of Engineering), and Mallory Meiser (COO). Boomerang makes simple, automated, affordable software for offboarding and alumni management, so companies without millions to spend can give departing employees the red carpet exit the best companies do.
In this conversation, Jeff gets into:
- The question he asked ADP’s HR team on his way out, and how it became Boomerang
- What a founder owes an acquirer, and how Boomerang’s seed came together
- What five years of channel deals at WorkMarket actually produced
- His unique process for introducing founders to investors, and why cold outreach doesn’t make the cut
Watch the full conversation below, or keep scrolling for the highlights 👇
A $20 billion company with no alumni motion
Jeff was leaving ADP when the idea for BoomerangHR surfaced. His first employer, JPMorgan, runs an impactful, well-regarded alumni program, so he asked ADP’s HR team what theirs looked like. The answer was … nothing.
“This is an organization with 50,000 employees with 20 plus billion in revenue, billions in profit. And they couldn’t figure out what to do.”
Non-competes kept the idea on the back burner for a couple of years. Once they ended, Jeff started interviewing HR leaders and kept hearing that alumni management is a nice-to-have, the kind of program no company is required to run. Sounds at first blush like a vitamin, not a painkiller. But the insight Jeff had was this:
“…Marrying (alumni management) with off-boarding started to move us to a have-to-have, because everybody has to off-board people.”
So Boomerang picks up when an employee heads out the door, plugging into a company’s existing HRMS and ATS to handle the exit itself, from compliance and COBRA to 401(k) rollovers, equipment returns, and exit interviews. AI agents, including an AI exit interviewer, do the work, so HR sheds the admin while the employee “actually feels more red carpeted out,” as Jeff put it. Afterward, the platform keeps verified alumni profiles and matches former employees back to open roles.
Jeff told HR Brew that “not a single one of our clients logs into Boomerang, ever,” adding that the system runs itself. Hundreds of companies use it today, representing millions of alumni, and customers include Cloudflare, SpaceX, McDonald’s, Priceline, the Golden State Warriors, Medline, and Hilton Grand Vacations. Its advisors include former CHROs and people leaders from ADP, Chipotle, Cisco, The New York Times, Coca-Cola, MongoDB, and Lattice.
Boomerangs (employees who leave and then come back, hence the name) are a big part of hiring. ADP research from March 2025, cited in HR Tech Feed’s coverage, found that they made up one-third of new hires. With cost per hire running 30%- 50% lower than that of hiring an external candidate (roughly $5k for non-executive roles and $36k for executive roles according to the SHRM 2025 Benchmarking Report).
What an acquirer is owed, and who got the next deal
I’ve written before about earnouts, and about how most founders who sell eventually start something new. For VCs hoping to back that next company, it helps to understand how a founder thinks during those years.
“ADP paid a lot of money for WorkMarket. They were owed the full measure of my effort for my time there.”
Jeff told ADP’s CEO he would run WorkMarket for the first year “as if you didn’t even buy it.”
“And what a gift is it to a founder to bring in your company, and we all know how we build, bubble gum and duct tape holding things together, and you just pray the thing doesn’t go down, and to watch as one of the most well-run companies, one of the most secure companies on the planet fixes everything you built.”
Having a front row seat to that, he said, was an unbelievable gift. After that year, the ADP exec who had been shadowing him took over as GM, and Jeff started to decelerate.
The Boomerang idea sat in the back of his mind while his ADP non-competes ran out. When they finally did, he never had to run a fundraising process.
“It was the people that hung around the hoop that knew when my non-competes ended that were the two that led this round.”
The two investors asked what Jeff was thinking about, he whiteboarded the idea, and both committed. Boomerang’s team came together the same way. Jeff had a crew he’d worked with before and, in his words, genuinely loves, respects, and admires, most of them out of WorkMarket. That group went on to build another company with Jeff as co-founder and chairman, sold it to Mediafly, and was wrapping up at Mediafly just as the non-competes ended. Jeff pitched the group on building Boomerang together, and as he put it, they “got the band back together.”
“We’ve got a reasonably high probability of having a nice stand-up double with the option value of having a grand slam.”
That’s how Jeff framed the opportunity for his investors. In the double, Boomerang keeps adding customers, holds churn at its current zero, reaches profitability on this round, and eventually sells. If a specific set of milestones hit, it raises a big Series A and goes after LinkedIn.
Five years of channel partnerships, zero dollars
Boomerang is a channel play. I’ve watched plenty of startups treat a big-name partnership as a go-to-market plan and flame out, so I pushed Jeff on it. WorkMarket had partnerships with Kelly OCG, Manpower, SAP, Allegis, and IQNavigator, and he asked me to guess how much revenue they generated over about five years. I took the bait and guessed $100 million.
“Zero. Not only zero million, zero dollars.”
A partner with 8,000 sales reps looks like an oasis in the desert, until you have to train those reps, incentivize them, route their leads, and support their customers. By default, they “couldn’t care less” about you. So Boomerang’s first channel partner is ADP, where Jeff knows the people running the business.
“They’ll forgive me for a mistake or two. The channel that doesn’t know you will not forgive you.”
A partner that doesn’t know you will drop you in a heartbeat the first time a rep loses a deal because your team wasn’t dotting i’s and crossing t’s. Jeff set his board’s expectations to match. With the ADP deal signed, he told them that “maybe two years from now, we’ll get dollar one.”
“That sales rep in Minneapolis, he or she’s got a thousand things to worry about today. How are you making their life better? How are you putting money in their pocket?”
How to actually get Jeff on the phone
“I respond to 0% of the cold outreaches I receive. Zero percent.”
Jeff does respond to 100% of requests that come through his network, whether it’s a friend vouching for a founder or a former WorkMarket employee. LinkedIn, he points out, is amazing at showing who knows who, so founders can find a mutual connection and ask for the intro. When they skip that step, he said, “the fact that you didn’t do that is crazy to me.”
When a founder impresses him, Jeff ends the call with an action item and pulls from his list of every investor he’s met who writes checks in the future of work.
- He picks the ones who fit (say, 17 of them) and has the founder flag anyone they’re already talking to.
- The founder sends back three to four sentences on the company and a DocSend link to the deck.
- Investors who want to meet ask for the intro, and the ones who aren’t interested can just delete it.
- Jeff emails each investor separately from his own account, with the founder BCC’d.
That last one (the BCC) stood out to me because of a recent intro Jeff attempted on my behalf. I didn’t realize I’d been BCC’d because almost nobody does it, so I replied as if I was CC’d!
“I want (the founder) to understand who was reached out to and when… They should be running a process.”
If another contact later offers an intro to the same firm, the founder knows Jeff already tried. When an investor passes with something substantive, like concerns about the space or a conflict, Jeff forwards that feedback to the founder. “I also want them to know that I said I was going to do something and I did it,” he said.
I shared a trick of my own. If an intro seems to have stalled, I’ll forward the email to the person directly with a note that our mutual contact said we should talk. It has gotten me meetings more than once.
“In this unbelievably AI slop filled world, the things that separate signal from noise are important, and relationships will always separate signal from noise.”
That was Jeff’s reply to my forwarding trick. It also explains how Boomerang’s seed came together and why ADP is its first channel partner.
There’s more in the full conversation, including the first company Jeff ran as CEO, which left him penniless and fielding a call from his mom about moving back home, the six other companies he’s been a co-founder and chairman of, and how Boomerang uses AI across its internal processes, from call recordings flowing into HubSpot to finance tooling. Watch it above.
