Ep 287 – What a Great CEO–CPO Partnership Actually Looks Like | Alex Coonce & Patrick Quigley, Sidecar Health

1. The best people leaders obsess over the business — not just HR

One of Alex’s strongest beliefs is that people leaders cannot design great talent systems unless they deeply understand how the company actually works. That means understanding the product, the customers, the revenue model, and the challenges the business is facing.

When Alex joined Sidecar Health, she didn’t just stay in the HR lane. Patrick pushed her into areas that felt uncomfortable — including joining sales calls and interacting directly with prospective customers.

At first, it felt strange.

But it quickly became one of the most valuable parts of the job.

“To be a great people leader, you have to learn the business. Become a student. Read everything you can, know your customers, know your sales strategy, understand your financials.”

The takeaway:
If you want a seat at the strategy table, start by acting like a business operator.

2. The CEO–CPO relationship works best when the role is bigger than HR

Patrick shared something interesting about hiring Alex: the moment he spoke with her, he knew she was another executive operator.

That distinction matters.

Too often, HR is hired to manage processes: payroll, hiring, compliance, performance reviews. But Patrick was looking for someone who could help shepherd the growth of the company itself as the team scaled rapidly.

“This felt like a real C-level executive.”

That shift changes the role entirely.

Instead of managing HR systems, the CPO becomes responsible for:

• Shaping culture as the company scales
• Helping leadership make better decisions about people
• Designing the operating system for growth

When that happens, the CEO–CPO partnership becomes a strategic one — not a service function.

3. If you want empathy for your business, put leaders in the front line

One of the most practical tactics Sidecar Health uses: forcing executives to experience the work their teams do.

Early in the company’s growth, executives would actually sit in customer service roles during open enrollment, answering calls from members trying to enroll in health plans.

It was uncomfortable — and incredibly valuable.

“It gives you so much empathy for what your team on the front line deals with. What are the hard questions? What pushback are they getting from customers?”

They also push executives to attend sales calls regularly.

Why? Because that’s where the real learning happens.

When leaders hear objections directly from customers, they understand:

• What messaging actually resonates
• Where the product is confusing
• What problems customers really care about

And that insight leads to better decisions across the company.

4. AI transformation is a culture challenge — not just a technology one

When the conversation turned to AI, Alex made a bold comment to the leadership team:

“If by the end of this year we have not completely transformed to AI-native, you should fire me.”

She joked about it later, but the point was serious.

AI adoption isn’t just about tools — it’s about culture. At Sidecar Health, they’re approaching AI in three ways:

Business impact

• How does AI drive top-line growth?
• How does it improve member experience?

Operational efficiency

• Where can teams automate repetitive work?

Cultural adoption

• How do employees think about using AI every day?

To encourage experimentation, the company:

• Gives everyone access to AI tools
• Encourages employees to share use cases in Slack
• Starts all-hands meetings with examples of how people used AI that week

The goal isn’t perfection — it’s curiosity and experimentation.

5. Career growth doesn’t always mean becoming a manager

One challenge many fast-growing companies face — especially lean ones — is that people expect growth to mean managing a bigger team.

But Sidecar Health intentionally keeps teams small.

That means the traditional career ladder doesn’t always exist.

Instead, they emphasize horizontal growth — expanding skills and exposure across the business.

“Career growth is not just up — it’s across.”

That might mean:

• Joining sales calls
• Working in a different function temporarily
• Building new capabilities outside your role

And in an AI-enabled future where organizations stay lean, this mindset becomes even more important.

Employees who expand their skillsets will have more opportunities than those who rely on the management ladder alone.

6. Passion and potential often beat “perfect experience”

One of Alex’s favorite leadership moments recently came from promoting an employee into a role they’d never done before.

They took someone with no prior sales experience and put them into a sales role.

Shortly after starting, he closed his first deal — faster than any new salesperson in company history.

It reinforced something Alex believes deeply:

“Passion and potential over just pure experience.”

Great companies create environments where people can grow into bigger roles — not just fill the ones they’ve already done before.

Because when you bet on potential, sometimes people surprise you.

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