Why executive engagement should be a CS priority

If you ask most CS leaders what keeps them up at night, the answers are probably familiar: retention, expansion, product adoption, impact. But there’s one layer above all of that – the stakeholders who actually sign on the dotted line.

That’s where executive engagement comes in.

In our recent Customer Growth conversation, Hook’s VP of Customer Tash Evans sat down with Sam Killip, VP of Customer Success at Attest, to talk about how her team has embedded exec engagement as a core part of Customer Success – backed by OKRs, cultural mindset, and smart internal alignment.

Whether you're trying to protect revenue, deepen relationships, or raise your team's strategic profile, these takeaways offer practical ways to make executive engagement part of your everyday motion.

Here are some of the biggest lessons from the discussion:

1. Executive engagement protects your value story

“In a challenging commercial landscape, the CFO, CMO, and CEO have to sign off a lot of the platforms and tools we’re providing. You want to make sure they are aware of you and the value you bring, and not rely solely on your users to sell that story upwards.”

Building rapport is just the foundation of executive engagement, but you also need to ensure your product’s value story reaches the people who influence budget decisions. When execs know who you are and how you drive impact, renewal conversations become a lot smoother.

2. Build your exec connections early

Sam also explained how, at Attest, their team takes a strategic approach to mapping C-Suite relationships from the start, especially for high-value accounts.

“When onboarding a new customer, we’ll often have our CEO send a note to their exec contact [...] even if it’s just a short message or a pulse report. That light touch helps build familiarity early on.”

Sam emphasized how CS teams should be encouraged to identify who had influence during the sales cycle and keep those relationships warm post-sale. Think of it as creating a distributed web of connections, not just relying on one or two champions.

3. Start small and build momentum

Executive engagement can feel daunting if you’re just starting out. Tash shared a simple, practical approach that any CSM can try:

“If I were starting fresh, I’d set a goal to engage execs in 25% of my accounts this quarter. I’d begin with new customers – where it’s easy to set expectations – and test from there.”

Start with healthy or new customers where expectations are easier to set. As you build confidence, expand to higher-impact accounts. Small, repeatable wins help embed executive engagement into your day-to-day rhythm.

4. Communicate differently with executives

What works for your day-to-day users won’t necessarily work for execs. Sam recommends taking a different, and more direct approach.

“Short, sharp, to the point – that’s always the way forward. Execs have a million things going on, and you’re not going to take up much space in their brain. So you have to be really clear on what you’re saying and why it matters.”

Sam's team uses pulse reports – brief updates (just 3–5 lines) sent from leadership to their counterparts – to stay visible without being disruptive. Even if you don’t get a reply, the message still lands.

5. Shift the mindset: You're not asking, you're adding value

One of Sam’s top tips was a mindset shift. Approaching execs shouldn’t feel like a cold ask. Remember, you’re there to add value, not extract time.

“There’s a natural reticence to reach outside our comfort zone. But if you flip the script and say, ‘I’m here to provide what this exec needs,’ it changes everything. Everyone wins.”

And sometimes, the best path to exec engagement is through your champion, helping them tell your story upwards.

Final thought: Understand what the business actually cares about

Sam wrapped with one of the most important points:

“Know what’s important to the business – and connect your work to those goals. That’s where exec engagement becomes meaningful, not just performative.”

It’s easy to focus on usage, health scores, or engagement metrics. But if you want to have real influence with senior stakeholders, your conversations need to reflect the outcomes they’re trying to drive. That’s how you move from delivering outputs to influencing outcomes.

Want to hear the full conversation?