A career measured in blank pages
On the Ashby One stage in San Francisco, Jacob Miller began with an old joke about a door. Before September 2022, he told the audience, anyone who signed up for Ashby had a fair chance of encountering him on the other side of it. He was the recruiting software company's first go-to-market hire, the fellow behind the curtain granting entry to what he called “super-exclusive Club Ashby.” The club was so discreet that it had 500 customers before it had what Miller considered a real website.
This is an unusual way to describe enterprise sales, an occupation better known for pipelines, forecasts and acronyms that reproduce in captivity. Yet the metaphor suited the moment. Ashby was still operating in stealth. Curiosity was part of the product experience. Miller checked the names, opened the rope and learned what prospective customers wanted before there was a polished public script telling them what to want.
Four years later, the curtain was gone. Nearly 700 people were in the room. Ashby said it served more than 4,400 customers. Miller had left the company and returned. Now, standing beside product manager Melissa Bierly, he was there to reveal the project that had occupied his second spell in the shadows: People Workflows, a system meant to organize the untidy succession of tasks that begins once a candidate signs an offer.
Three first drafts
Miller's career makes more sense when read as a preference for first drafts. After development work at Casa Esperanza Homeless Center, he entered software sales at Citrix in 2013. There were turns through inbound and outbound sales development before he became a corporate account executive. It was an education in an established sales machine. His next moves took him closer to the point before the machine exists.
At Growbots, he arrived as a founding account executive, then became a team lead and a player-coach sales manager. At Airbase, he was again a founding account executive before leading sales development. A colleague from Airbase, Tushar Makhija, later recalled being one of Miller's references when he interviewed to become a founding AE at Ashby. By April 2021, Miller had joined as Ashby's first sales hire and its second nontechnical employee.
“Founding AE” is a title that sounds grander than its daily reality. It means selling a product while the language around it is still wet. The rep must discover the buyer's problem, test the company's explanation of that problem, and notice which promises the product can actually keep. At a mature company, salespeople inherit a map. The founding account executive is asked to sell tickets while drawing it.
The route to Ashby's new-product desk
The company that outgrew his favorite stage
Miller has been candid about his native habitat. He considers himself an early-stage person and has said that, once a startup passes roughly 100 employees, he tends to get antsy. Ashby became the exception. In a reflection written while still at the company, he said it was the longest he had remained with a startup. The obvious explanation was “the people,” but he found that answer too generic to be useful.
So he told a story from a company offsite. For 90 minutes, Ashby employees gave lightning talks of less than five minutes each. The subjects included Rhode Island as a tourist destination, the life-consuming properties of 3D printing, and the mystery of human consciousness. Halfway through, a colleague texted him: “this right here is Ashby culture.” Miller agreed. He saw a room full of colleagues being intelligent, funny, curious and unapologetically interested in things beyond their job descriptions.
Culture is a word that startup companies have polished smooth through overuse. Miller's anecdote gives it some texture. Nobody was aligning on a quarterly objective. Nobody was unveiling a value printed in tasteful sans serif. They were explaining lobsters, plastic filament and the mind. A workplace had made room for its people to be specific.
“I left chasing the thrill of 0→1, and realized the team and culture I cared most about were already here. Feels good to be home.”Jacob Miller, announcing his return to Ashby
A departure with a return address
Still, the early-stage itch won for a while. Miller's first Ashby chapter ended in early 2025. Later that year, he returned with a title designed to conceal as much as it disclosed: GTM Specialist, New Products. He described himself as Ashby's first rehire and revived his original new-employee introduction slide for a team that had grown substantially since 2021.
His announcement borrowed the old club image. He had once compared first-sales-hire life at a stealth company to working the door of an exclusive venue, letting a few people in and keeping the rest behind the velvet rope. “Turns out I wasn't done with that gig,” he wrote. Anyone curious about the project could send him a message. He might tell them. The tease worked because the mystery had a history.
Returning can look, from a distance, like retreat. Miller's version reads differently. He did not come back to repeat the original job. Ashby had become too large to recreate its 2021 conditions, so it created a small frontier inside itself. Miller returned to the part of a company where questions still outnumbered processes. The organization had grown; the assignment was young.
What happens after yes
People Workflows begins with an awkward fact about hiring: companies lavish software and attention on candidates until the offer is accepted, then often send them into a fog of inboxes, tickets and reminders. The recruiting team has crossed the finish line. The new employee, rather inconveniently, is only at the beginning.
Miller described the gap onstage. A recruiter might keep someone closely informed through interviews, only for communication to fall quiet between the signed offer and the start date. Hiring has defined stages, dedicated systems and visible owners. Onboarding can become a relay race in which several runners are still looking for the baton.
The product he presented enrolls a new hire into a custom journey once an offer is signed. A workflow can request information, initiate a background-check integration, assign equipment tasks, send communications, handle regional variations and surface anything blocked. The aim is not to remove people from onboarding. It is to remove the scavenger hunt from their calendars.
After the offer, the handoff stops being invisible
“The workflow runs in the background, and you step in where it matters,” Miller said when the product launched. It is a compact philosophy for automation. Good software should absorb repetition while leaving judgment, welcome and care in human hands. The system handles reminders. Nobody has ever felt warmly received by a reminder.
The assignment also fits Miller's history. A founding seller lives at the seam between a product and the people expected to use it. He hears the polished intention from one side and the inconvenient daily reality from the other. People Workflows is almost entirely seams: recruiting to people operations, people operations to IT, signed offer to first day. Its material is the handoff.
The useful trick of starting again
In 2024, Miller looked back at a sales organization roughly 20 times larger than the team he had started alone. What pleased him was not merely the multiplication. He believed buyers were still encountering the sales values that had attracted him at the beginning. Growth is easy to count and hard to recognize. A headcount number rises neatly; the character of a conversation does not come with a graph.
Customer recommendations point to the behavior he values: curiosity, listening, useful introductions and an absence of pushiness. Those qualities are not ornamental in a market as personal as recruiting software. An applicant tracking system stores decisions about people. Selling one requires fluency in process, but also some respect for what the process contains.
Miller's public voice adds mischief to that seriousness. He collects product details under the tag #ashbyhiddengems. He talks about curtains, clubs and working in the shadows. When People Workflows finally emerged, he compared his waitlist duties to standing at the door of Berlin's famously selective Berghain, while promising Ashby would be slightly less exclusive. Enterprise software rarely suffers from too much personality.
His career now forms a tidy loop without becoming a closed circle. Citrix taught him an established system. Growbots and Airbase put him at the founding AE desk. Ashby gave him a company without a public website, then a growing sales organization, then a reason to leave. His return supplied the last useful complication: sometimes the pursuit of novelty is less about changing the logo on the laptop than changing the problem in front of it.
Onstage, Miller said he occasionally missed the stealth days. It was a charming admission, but nostalgia was not the product being sold. He had found another curtain to stand behind, another door to open, another first draft requiring a reader. The club had thousands of members now. There were simply new rooms.