There’s a classic book-title-turned-phrase, “What got you here, won’t get you there,” and it certainly holds true in startup land. The actions, people, systems and processes that got you from 0 to 1 are unlikely to be what will get you from 1 to 1000. And unfortunately, this can mean leaders coming in and out faster than you expected. Systems breaking down. Processes no longer working. But it’s not all doom and gloom.
With growth, you get the opportunity to right the ship. Even though this inflection point can feel painful, it’s one of the best times to bring in a fractional leader like Hello Generalist member Karen Chi to help make the transition a little less choppy.
I had the great pleasure of speaking with Karen to get her perspective on bringing in part-time revenue leaders, and how to set them up for success. Karen was a long-time sales leader at LinkedIn, and VP Sales at Cameo. Today, she works as an Investor, startup Advisor, and Fractional CRO for early-mid-stage B2B startups.
On a personal note, I’m a glutton for stories of windy careers. Karen started out in enterprise systems consulting before transitioning into operations management. Then, she spent nearly 10 years working her way up at LinkedIn, jumped over to lead Cameo’s sales through their hyper growth, and had now has totally pivoted into fractional, investing, and advising. A true generalist in that her expertise is built by a variety of professional perspectives. (If you’re into this kinda thing, check out The Pathless Path by Paul Millard — a great weekend read full of windy path inspo.)
But, what I found most striking about her was the emphasis she placed on vulnerability, trust-building, and communication as the hallmarks of successful work, whether that’s fractional or full-time. I think you’ll find some real gold nuggets in our conversation. Enjoy!
Drop 1. Thinking about hiring a part-time CRO? See if there’s been a point of agitation
The role of a fractional CRO is someone who can connect functions and string together a number of different initiatives across customer acquisition and customer growth, from marketing, sales, and customer success. In my experience where I’ve worked with clients, there’s been some sort of agitation. The company has either had a previous CRO or head of sales and something did not work. Or they’re growing too quickly. There’s a bit of a turnaround situation that needs to happen – that’s a really clear why for a fractional CRO or head of sales to enter the scene.
Take it back to your team:
- Is your company going through an inflection point where sales are growing faster than the systems that can manage it? Do your sales and marketing orgs feel a vacuum in leadership?
- Are initiatives falling through the cracks and your GTM organizations no longer feel on the same page? Talk to your team about the pain they’re feeling.
- Agitation isn’t a bad thing. It’s a good signal to let you know that it might be time for you to bring in a leader.
Drop 2. Be explicit in your communication…and ask about the sacred cows
I ask questions about the sacred cows. The unsaids of why was that person hired or the unspoken rule around why we do this the way we do. Awareness is important. A big part of my job is to ask the dumb and tough questions. Especially in the early stages as I’m looking to build trust quickly with the team, having social awareness is important. That’s why I ask about the unspoken rules.
Take it back to your team:
- Karen quickly gets vulnerable and asks the hard questions of her founders and team members about their hidden skeletons. Ask your team if there are old processes that no longer make sense for your organization.
- Trust and vulnerability are key to creating change. Karen comes in from a place of curiosity, letting people know that she’s trying to understand why things are done the way they are. See if your team is comfortable sharing the sacred cows and the honest truth.
- Consider hosting a roadshow or listening party as Karen does, with the pure objective of developing awareness and understanding. You might be surprised by what comes out and what new initiatives can be developed as a result.
Drop 3. Your customer can unify your teams
Bring the constant drumbeat of centering the customer. For companies where they’ve grown rapidly and functions have become siloed, everyone can relate to the customer. It’s a really strong way to unify perspectives. We’re bringing a customer-centric lens to what we’re doing, from revenue, customer, employee, we’re bringing those lenses to mutually help define and make decisions that can oftentimes be really challenging.
Take it back to your team:
- If you’re having trouble making a decision with what initiative to prioritize or what direction to go, go back to your customers. Let them guide you.
- Ask your different teams what they’re hearing from customers in their sales calls, feedback sessions, and customer support tickets. See if there are common threads to give you a north star.
Drop 4. How to set up your part-time leader for success as a founder
One of the ways to set me up for success is clearly communicate that this change is happening, a fractional CRO is coming in, and here’s what I’m looking for her to help us do. The phrase, “What’s gotten us here is not going to get us there. And one of the ways we’re going to get there is that I’m bringing on Karen to help us with Z, Y, Z,” clearly sets expectations. It also gives folks permission to raise concerns, think about how a resource like me might be able to help them, anticipate change and embrace it.
Take it back to your team:
- Change and new leadership can be a hard pill to swallow for your team. Let them in on the why’s and what you’re hoping your fractional leader can accomplish.
- Don’t forget to present your part-time leader as an ally. They’re there to help, and that involves org-wide collaboration. Make connections and introductions for them.
- Your people have the greatest institutional knowledge. Create an environment where both your part-time leader’s expertise your team’s tribal knowledge can be leveraged.