Matthew Iacovelli

A Designer Who Ended Up in Hiring

Iacovelli's academic background is in industrial design. By the time he was graduating, his interest had narrowed to theoretical design, the study of processes and systems and how they interact with one another. It is an abstract discipline with a very practical implication, one he grasped early: to actually change how a system behaves, you have to reach a position inside an organization where you can move it.

So he applied broadly, and landed at Talroo, a job advertising and recruitment marketing platform, as a business development representative. He was one of the first two BDRs on the team and helped build the entire function out from there. He then moved into an account executive role, carrying some of the largest companies in the space as customers. Almost by accident, he had found the intersection of two things he cared about: complex systems and the people trying to navigate them.

The move to HeyMilo came through a mutual friend, when co-founder Sevation reached out during a period when Iacovelli was open to what was next. He liked the founder immediately, and more importantly he recognized the product as the logical continuation of the problem he had been staring at for years in recruitment marketing. He joined as the first sales rep on the team and has since grown that team out around him.

Learning From the People on the Other Side of the Table

Ask Iacovelli who shaped him and he does not reach for a single name. He reaches for a category. "The people that I've learned from most are actually the people that I've sold to," he says. Large customers, over years of conversations, taught him how to sell and how to carry himself in the community, largely by teaching him how to listen first.

Thad, the CEO at Talroo, gave him his first exposure to solution selling as a discipline rather than a slogan. Watching Thad think about product and about delivering for customers showed Iacovelli something he had not seen before: design thinking applied to a sales environment, product logic and buyer needs treated as one continuous problem instead of two departments.

At HeyMilo, co-founders Sevation and Ramy have compressed years of learning into roughly twelve months. Iacovelli calls them two of the best people leaders he has met in the industry. Ramy, the CTO, moves across engineering, sales, and customer success with his hands in every process, an approach that has visibly unlocked talent throughout the organization. Sevation reads the community, tracks where the market is heading, and pushes on how the company develops its own people so the team is genuinely ready when it gets in front of the customers who need them. "At the end of the day, we want to be as successful as possible," Iacovelli says, "but as long as the organization helps people and we're able to get in front of people to support that, like, we're all about that."

There is one more group he credits, and he is only half joking about the label. He calls the reps who report to him his bosses. The step from individual contributor to director, he says, is a completely different job, and it made him more of an employee than ever, not less: reporting up to leadership and down to his team at the same time, running a constant feedback loop of how can I support you, how can I help you, how do I make sure you are as successful as you can be as a person.

Augment the Recruiter, Never Replace Them

Iacovelli has spent the past year at the front edge of AI in hiring, and he is impatient with the assumptions on both sides of the debate. HeyMilo is AI native in how it builds and how it operates, including on the go to market side, where the team lives in Claude and Cursor and treats the tooling as an extension of their own capability rather than a substitute for it.

On the core question, he is unequivocal. The dominant use case he sees among customers is augmenting the recruiter experience, not eliminating it. "You need the human connection," he says. Nobody buys from a robot, and nobody makes a life changing decision to leave a company they have known and trusted for four years because an AI suggested it. What the technology can do is give the candidate a real conversation instead of a black hole, a chance to speak to an organization and understand the role rather than disappearing into silence.

That matters most, he argues, for the people the old system fails. Not everyone is a great resume writer. Not everyone has $200 to pay someone to rewrite their resume so it clears an outdated, keyword based grader. AI, used well, lets employers actually learn something about the candidates in their funnel, efficiently and at scale. Candidate skepticism is real and he does not dismiss it, but he sees the objection shrinking with the technology's quality. Three years ago the organization's CSAT scores were significantly lower than the 4.5 to 4.6 out of 5 they run at today, a shift he attributes both to better technology and to a changing workforce that is increasingly comfortable with it.

More Light in the Room

The same logic applies to how Iacovelli runs his own team. He has never been able to sit in on every rep's call simultaneously and deliver constructive feedback in real time. Now Cursor pushes a notification into Slack summarizing what happened across his reps' calls that day and flagging gaps against the team's sales methodology, and he can coach on it immediately, because for the first time he has both the data and the means to act on it.

He is equally candid that moving into management came without a playbook, and that having AI as a companion for the small daily decisions has let him grow into the role faster than he otherwise would have. He does not pretend the transition has been frictionless. "Do I walk in the dark room and trip on all the furniture? Yes," he says. "But there's more and more light for me to walk through."

His verdict on the technology is deliberately unglamorous. Is AI the ultimate god of reality, changing everything? No. Will it drive the industry forward, help organizations learn more about people, and change the dynamics of how job seekers find work that actually fits them? On that he is confident. The end state he wants is a hiring process that has become a people conversation rather than a system quietly kicking applicants out with no conversation at all. As for how he got here, his own account is characteristically plain: step by step, he says, he simply tried the hardest that he could.