From the Commercial Side to People Leadership

Lynne Hamilton, Head of People, Inspiren

While functional expertise plays an important role early in our leadership journey, as we grow in our career, it becomes more important to lead at the organizational level. This requires a whole different set of skills and expertise. While many leaders follow a functional path to senior leadership, there are exceptions like Lynne Hamilton who transitioned from a commercial leader to SVP of People and Partnerships at Black Crow AI. I wanted to know what that experience was like.

We talked about:

• Founding Black Crow AI

• Transitioning to the people function

• The importance of one-on-one interactions to drive engagement and performance

• The skills she used from her commercial background in a people role

• Why Black Crow AI has a four-day work week and how they make it work

Can you tell us a bit about yourself?

I'm Lynne Hamilton, a founding team member overseeing the people team at Black Crow AI. We're a 60-person series A startup specializing in AI machine learning, helping DTC companies optimize their customer journeys.

Instead of giving you my resume, I'll share what drives me. First, I've never done a job for which I'm qualified on paper. My mom was handicapped due to a car accident before I was born. I watched her tackle daily obstacles with ingenuity, which taught me never to be afraid to try something new or unconventional.

Second, my family business is teaching - aunts, uncles, grandparents, parents are all educators. I grew up with a love of learning and people who were great at understanding audiences and explaining things in multiple ways - an important leadership skill.

Third, I've always intentionally worked with great humans. I spend most of my waking hours with colleagues, so enjoying their company brings joy to my days.

On the resume side, I've spent 20 years in nonprofits and startups, with about 15 years in the AI world, primarily on the commercial side - customer success, sales, and marketing. I moved to the people side with Black Crow about two and a half years ago.

The ability to figure things out in unconventional ways must have had a huge impact on your work today.

Definitely. It was my mom's joy in solving problems that inspired me. That attitude and skill set have been really helpful, especially in smaller organizations full of challenges, unpredictability, and complexity.

Founding Black Crow AI

After being on the commercial side for many years, what made you join Black Crow AI and then move to a people role?

Lynne: I helped found Black Crow alongside a decent-sized founding team. We’d said goodbye to a previous company during the pandemic, and I didn't want to stop working with these people. I loved our tech stack and machine learning AI and wanted to rebuild it in a different way.

When we closed the other company, I personally laid off 30 people. It was a year of grief, but the dual mission of working with people I valued and bringing our AI to life kept me going through that difficult period.

How many of you founded it, and how big are you now?

Lynne: About 12 people founded it, and we're now at 60. I love this headcount range of 50-75 people - there's diversity and energy, but you still know everyone's name.

Transitioning to the People Function

What inspired you to move to a people role rather than staying on the commercial side?

It had always been my calling, but I ignored it because I was good on the commercial side. Honestly, the prestige, centrality to business strategy, and money kept me away from the people side. But I genuinely love people - emotionally and intellectually. I love the subject of people, brains, personalities, empowering them, and having real conversations. The gravitational pull was finally too strong, and we needed someone to establish the people function.

I came over with credibility as a senior executive from the commercial side, which gave me immediate clout in the people function. I wanted to stay central to business strategy, and the team wanted that too.

The heart of managing people - driving value for them, understanding market feedback, building relationships - it's very similar to the commercial side.

Were there transferable skills from the commercial side that you brought to the role?

Absolutely - analytical thinking, strategic brain, and understanding retention. On the customer success side, you think about retaining customers, their expectations, and what they're getting. I approach employees the same way.

I hired a brilliant recruiter named Kelsey, and while I didn't know the technical side of recruiting, I knew sales motion and sales funnels. I knew the importance of a data-driven funnel, how to craft messaging, and move people through different stages of a process.

The heart of managing people - driving value for them, understanding market feedback, building relationships - it's very similar to the commercial side. I did an okay job commercially, but my heart wasn't in it. Now it's fully engaged.

We don't see the people team as a service function - that's doing it wrong. A people function should drive performance and retention, bring in and keep incredible talent.

Building the People Function

I'm the caretaker of our most valuable product - Black Crow, the place to work. That's my mentality. My customers in recruiting are giving me their careers, committing years of their life to us.

We don't see the people team as a service function - that's doing it wrong. A people function should drive performance and retention, bring in and keep incredible talent.

We'd be nowhere without our talent. Sometimes I joke at company meetings when we hit financial milestones, "You're welcome, guys!" because I brought everyone in. That's my million as much as any other function's.

It's key that you think about it as a product rather than having a paternalistic approach common in older HR models. It’s a different approach.

Yes, and in sales and customer success, you play a one-on-one game - getting in front of customers, having conversations, building relationships. I bring that one-on-one approach to the people function. And I insist on it from our exec team as well and our leaders. Retention is absolutely a one-on-one game. Driving performance is also a one-on-one game. Our exec team and I meet with every employee twice a year, just one-on-one, to have a conversation. That commercial mentality has really shaped how I approach the people side.

I remember on the commercial side, in sales, in particular, making your quarterly call or even on the customer success side. If something doesn't go through, you lose a customer and you hadn't given any heads up, is the worst offense. That’s similar to how I feel about our team. We're obviously going to have regrettable attrition. People that we love are going to move on. But if we had no clue, that's how we know there's like really big issues in the organization. The one-on-one game helps you stay on top of that. So when that's regrettable, it's regrettable, but we know why and we tried to address it. Or we couldn't address it and we have a better transition plan, but it really, it just helps the whole life cycle for a person working at Black Crow is just so much better if you, if you're having those conversations.

What was the transition into your role like?

It felt natural in a lot of ways. Being in position to lead our org just felt great and felt right and authentic. so a lot of the big picture, that was very natural. But there was still a lot to learn, there’s so much expertise in the people function. There's depth of knowledge in every kind of functional space. so I ended up Googling a lot and going on TroopHR and asking lots of questions and doing research. I want my CEO Richard to know that it's based on X, Y, and Z because he knows I have no people experience. So it's not like I'm hiding anything. I think what was most important, which was a lesson I learned later in my career, was not being afraid that I don’t know.

I also have this incredible mentor, Rebecca Price. She's one of our leads in our series, a seed stage and one of our investors. She took me under her wing and we met really regularly. I think we met weekly or bi-weekly for a very long time to beef up on all of that missing information.

I love that. There is a difference between functional leadership and organizational leadership. Functional leadership is what you need to run a function while org leadership is what you need to help run an organization. A lot of people lean more on functional expertise. I think because you didn’t have it, you thought about how to help lead an organization.

Yeah, I was listening to Edwina Johnson on your podcast. She was talking about her role as a COO. And she said the business is my client – she looks at ways to enable or multiply the output of the rest of the organization. I feel similar to that. I try to embody Black Crow and think about what is in its best interest. I take that mentality in talking with our exec team. It helps drive decision-making certainly and then it helps do some of the harder things as a leader.

How has your role evolved since you started?

I've started to lean more toward the planning side of the organization. I lead our weekly executive team sessions, drive the cadence for forecasting, financial strategy, and planning. I just led an H2 forecast exercise and manage our OKRs and goals.

It's morphing toward the chief of staff to the CEO side, partly because we have a good people practice established that doesn't need as much attention, and our planning side could use more leadership. My diverse background helps me flex in this direction, which I find equally interesting.

How big is your people team now?

It's just me and my recruiter Kelsey. We outsource some functions, and finance handles payroll and benefits administration. I actively avoid bringing some of that detailed work onto my team - details aren't my strength. I'm perfectly happy to ensure our team gets paid the right amount using someone else's strengths and talents.

Our "Fridays are yours" policy is a huge piece of getting the best out of people. Burnt-out people are terrible at producing value. People do better when they're energized, focused, and sharp.

The Four-Day Work Week

You mentioned that your organization has a four-day work week. What's it like leading an organization with that policy?

This is my soapbox topic! It's driven by our most important core value: "human first" - not people first, but human first. Our CEO Richard is emphatic about recognizing the physical humanity of who we are - that we need to eat, sleep, connect with others, that we have productivity spikes, bad days, emotions.

The other driver is doing what's best for Black Crow - getting the most productivity and highest performance from our team. Our "Fridays are yours" policy is a huge piece of getting the best out of people. Burnt-out people are terrible at producing value. People do better when they're energized, focused, and sharp.

We need people who aren't distracted by stress from unscheduled appointments or lack of connection. Fridays are yours sets people up to flex and recover so they can perform better.

During onboarding, we explain that the business makes no demands on Fridays - no meetings. You can choose what to do based on your goals and personal needs. Some team members never work Fridays. I have two small boys, so I use Fridays to decompress and get my work house in order. What we see in every function is people coming in Monday focused, energized, and smart. Nobody's job is a four-day job at Black Crow - these are full-time positions. We've done amazing things, because within a traditional work week, there's so much waste when people are tired or burnt out.

People often overcomplicate having a four-day week, wondering how to know if work is getting done.

We're very outcome-driven. Everyone has goals and is responsible for them. We coach on inputs - how to prioritize better, set up your days better, have a better pitch call - but focus on outputs. We don't care about what hours you're working.

We all work together Monday through Thursday to collaborate and feel like a unit, especially as a remote organization. You need structure and crossover time, but not all the time.

It's not perfect - we have customers who work on Fridays, and some of our team does check email then. There will be moments where we need to work on Fridays, but when we ask the team, I know they'll show up because it's not about hours - it's about doing amazing things together.