People developing people: Build a culture worth bragging about (even after employees leave)

Insights from Rachel Kohn, Senior Vice President of People Operations at Sendoso

Electives Co-Founder Jason Lavender sat down with Rachel Kohn, SVP of People Operations at Sendoso, to learn how she's building a company culture that earns loyalty long after people leave. The conversation covers the listening tour that changed her approach, a dramatic eNPS turnaround, and why she believes more People leaders should be driving AI adoption.

Key topics covered:

• Why planning for people to leave makes today's culture stronger
• How a listening tour builds trust before any program does
• The Ask Me Anything ritual that shifted employee-leadership trust
• Taking an eNPS from -19 to a consistent +35 to +40
• Why AI literacy belongs in the total rewards conversation

Putting people first is a practice, not a given

Rachel Kohn came to People Operations the long way: Teach for America, kindergarten teaching in New Orleans, college admissions, talent acquisition for charter schools, executive search for Boston tech companies and eventually into a People leadership seat through an acquisition. That background shapes how she thinks about what makes companies truly functional.

“Companies that are better at developing people are the ones that actually put their people first. Investing in your people and making sure they're successful pays dividends on your top and bottom line. It's also what makes your customers happy — when people genuinely enjoy their work and feel like what they do every day is meaningful, that shows up everywhere.”

The inverse, in her view, is companies that lead with product or financials and treat people as secondary. The outcome tends to show up eventually, in engagement scores, in attrition, in customer satisfaction. For Rachel, it's not theoretical. She's seen both sides.

The “alumni culture” mindset

Rachel has a north star that sounds counterintuitive at first: she's building a company culture that people will brag about after they leave. Not just while they're there. After.

"I love the alumni culture that comes from: ‘I worked at this company. ‘I had the best time working there.’ ‘I would return there.’ Or ‘I would continue to recommend it as a great place for people to work.’ That is really what gets me out of bed."

She's clear-eyed about modern careers. The 30-year tenure is gone. So instead of treating that as a loss, Rachel treats it as a design principle. If people are going to move on eventually, the job is to make the experience worth something lasting. She points to what's happened in Boston's tech ecosystem, the HubSpotters, the Wayfair Mafia, the Klaviyo alumni, as proof that companies with powerful alumni networks got there by building something people genuinely wanted to be part of.

Sendoso added a direct question to their quarterly engagement survey to track it: I'm proud to work at Sendoso. The current response sits at 8.7 to 8.9 out of 10. Rachel intends to keep pushing it.

Be a business partner first

One thing Rachel is deliberate about: People leaders earn influence by showing up as business partners first. That means understanding the functions they support well enough to actually help them, rather than just running HR processes.

"For better or worse, I meet with 25 leaders over the course of the month, and then my direct report meets with the rest of the team, because we believe that being a business partner first matters a ton."

At a company with a lean People team supporting 230 employees across 37 states and 9 countries, that cadence requires prioritization. But Rachel sees it as foundational to having credibility. You can't diagnose what your people need if you're not in regular conversation with the leaders who manage them.

Start with a listening tour, every time

Rachel's single most consistent piece of advice for anyone building a learning culture: don't start with programs. Start with listening.

She's earned this opinion the hard way. Earlier in her career, she admits she walked in convinced she already had the answers.

"Earlier in my career, I absolutely fell into that trap — coming into a company convinced I'd seen it all and had all the answers. I got a rude awakening pretty quickly: I needed to listen more."

The listening tour is the mechanism that makes programs actually land. At Sendoso, the best initiatives they've implemented came directly from employees, surfaced through quarterly engagement surveys with structured space for feedback. What makes it credible is the step that follows.

"You build trust by hearing people and then actually acting on the feedback they give you."

Hearing isn't enough. The feedback loop only closes when people see their input turn into something real.

The “Ask Me Anything” that changed trust

One concrete way Sendoso shifted its culture is a 10-minute Ask Me Anything at the close of every monthly All Hands. Employees submit questions anonymously, or with their name if they choose. The leadership team answers live, with no prep and no cherry-picked questions.

"Sometimes the questions are tough, sometimes they're softballs. Either way, we hold the space. You can ask us anything and we'll answer it live, unscripted and unprompted."

When the team doesn't have a complete answer, they say so directly and commit to following up. That honesty has turned out to be more trust-building than polished non-answers ever could be. 

Combined with sharing real business metrics at every All Hands (targets, where they're hitting, where there are still gaps), the leadership team fundamentally changed what employees know about the company they work for.

"Our employees are incredibly smart individuals, right? Let's give them more information and help them understand it so they can really understand where the business has been, where the business is going and what we're striving towards."

From -19 to +40: The eNPS turnaround

When Rachel joined Sendoso via acquisition two and a half years ago, the employee Net Promoter Score sat at negative 19. Today it runs between +35 and +40, quarter over quarter.

"That didn't happen overnight. That happened over the course of two and a half years, and that happened over the course of us holding space for people, giving them the opportunity to really say the things that they wanted to say without fear of retribution."

Over time, employees saw that speaking up was safe. That hard feedback didn't trigger retaliation. That the leadership team wasn't afraid of the truth. And that something would actually happen as a result of sharing it, even when the response was simply acknowledgment.

"Even if the action is a simple ‘we hear you.’ And we either can or can't do something about that, but you need to know that you're heard."

Sometimes the most powerful response isn't a solution. It's an acknowledgment.

AI literacy belongs in total rewards

Rachel's take on the evolving role of People leaders has a sharp edge to it: AI adoption is a people and culture opportunity, and People leaders should be driving it.

“A lot of people leaders are on the forefront of leading the AI revolution within their companies. Part of that is because education, learning and development and AI literacy are all part of the investment in their people — and increasingly, part of the total rewards statement too.”

At Sendoso, this shows up in three concrete ways. An AI Steering Committee, with representation from finance, people, customer success, engineering, product and legal, has been running for three quarters. The committee is working to align on tools, shared language and direction. 

AI peer learning circles are launching this quarter, co-led by an internal CSM-turned-go-to-market engineer who builds agents and volunteered to host office hours and show-and-tells. And Rachel's remit for this quarter is building AI fluency and literacy models by department, defining what "developing," "proficient" and "advanced" actually looks like for each function.

The benchmark the leadership team set at their last offsite is deliberately human-scale:

"If every person at Sendoso can have some process that they have now automated, that they used to do manually. We'll consider that a success. And that will be our first benchmark; let's get people comfortable knocking a manual task off of their daily task list."

Address the fear directly

There's a real, understandable anxiety running through most employee bases right now: if I get good at AI, does that make me more replaceable? Rachel addresses it head-on rather than minimizing it.

“That's why we keep coming back to this conversation: getting good at AI, or implementing it across our work processes and how we show up day-to-day, doesn't impact your job in a negative way. It ultimately helps you be better and more productive. That's the goal."

The framing she keeps coming back to: not "do more with less," but "do more with more." AI isn't a cost-cutting measure at Sendoso. It's capacity creation. It's bandwidth recovery. It's freeing up cognitive space to focus on the work that moves the needle.

That framing shows up in specifics. Rachel's team is building an internal HR bot this quarter so that when employees ask where to find their W-2, they get a step-by-step answer instantly, without a ticket or a Slack message to the People team. It's a small example, but it's the right one to start with.

"All teams run leaner than they'd like. That's where AI comes in for us. We always ask: how do you do more with more, rather than more with less."

The goal isn't efficiency for its own sake. It's recovering the time to focus on the work that requires a human, the coaching conversations, the trust-building, the culture work that no bot can do.

Connection and joy are part of the work

Sendoso is remote-first, with roughly 230 employees across 37 states and 9 countries. Building belonging across a dispersed team is as much part of Rachel's job as building skills. When an employee mentioned in an engagement survey that they missed a virtual happy hour, Rachel took it seriously.

"That told me we gotta really get on: how do we foster more connection and joy for people in a remote-first capacity."

The response was a curated calendar of monthly experiences, some hands-on, some just for fun, designed to give people a brain break and create genuine moments of connection outside of work channels. This month: origami with an Electives instructor, timed with Mental Health Awareness Month.

It's a small thing. And it's exactly the kind of thing that makes someone say, years later, I loved working there.

Build something worth being proud of

Rachel's work at Sendoso is proof that culture change is a system, not a single initiative. It's listening tours and quarterly surveys and Ask Me Anything sessions and transparent All Hands and peer learning circles and human-scale AI benchmarks and origami for a remote team.

None of it happened by accident. All of it came from listening first, then acting.

The north star is deceptively simple: build a place people are proud to have worked. Get that right, and the eNPS, the engagement, the AI adoption, and the alumni network tend to follow.

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