Twine’s Ten(ish) Tips with Colleen McCreary (CPO @ Credit Karma)

Connor Swofford
Twine Labs
Published in
5 min readAug 26, 2020
Colleen McCreary, 4x CPO

AN INTRODUCTION TO COLLEEN

Colleen is a four-time Chief People Officer who’s led through international hypergrowth, M&A, and multiple IPOs. She’s currently the Chief People Officer at Credit Karma, and has previously led the people teams at Vevo, The Climate Corporation, and Zynga. She was also a technical advisor to the HBO show “Silicon Valley.”

We have a far-ranging conversation on following your curiosity, picking the right CEO to work with, and — my personal favorite — differentiating pattern matching from scar tissue.

Joseph Quan | CEO & Founder, Twine

What advice would you give to a first-time Chief People Officer?

The best piece of advice I have is “Remember the business of the company.” It’s so easy to get caught up in solving the immediate HR and recruiting problems in front of you. But remember — at the end of the day, the business of the company is what matters most.

You can’t expect to lead effectively if you don’t connect the metrics of the business back to your functional realm of responsibility. Throughout my career, every [people/HR] initiative I’ve worked on, I’ve directly connected back to the success of our core business.

How do you keep the business at the forefront of your mind, with all the pressing day-to-day issues you deal with as CPO?

I’ve always been naturally curious about the business; I’ve always wanted to pull up the bigger picture. It’s a habit that made me stand out early in my career.

Take recruiting for example — as soon as I’d start recruiting for a role, I’d ask a ton of questions:

  • Why are we hiring for this role?
  • Why now?
  • How will hiring this person impact the future of the company?

Not only did getting this information help me sell the candidate, but it also helped me understand my job in the broader context of our business.

My whole life, this natural curiosity has helped guide me. I realized that knowing IT, marketing, sales actually made me better at my job. And sometimes it was just to win arguments — but it paid off [laughs].

That intellectual curiosity has always guided me and led me to always say yes. I took on lines of business no one else was interested in. I went to Hyderabad when I had a 3-year old son. I took an HRBP role after a long time in recruiting, even though I was dead set against HR.

By following that curiosity, you set yourself apart. And for better or worse, the bar for having a lot of cross-functional experience as a “people/HR person” is pretty low here. It’s essentially skills arbitrage.

If there were a Colleen McCreary playbook to building a great relationship with your CEO, what would be in that playbook?

It all starts with the interview process — I use that to set the foundation for my partnership with the CEO. It’s often a 4–6 month process, mainly driven by me as a candidate.

It’s fed by my curiosity, my desire and need to understand who the CEO is, what they’re motivated by. It tells me what working together will be like. It really is similar to dating. You’re building a long-term partnership and you need that compatibility to make it work. You must be authentic throughout that process.

Take my time at Zynga — where I eventually took the CPO role — for example. When I was originally approached by the founder/CEO, it was clear that he was just trying to check the HR box — he just needed someone to fill the seat.

On that intuition, I turned the job down a couple times, because I didn’t get the sense that he valued this partnership, or even understood what a strategic people function meant. It wasn’t until the company really proved they were committed to investing in people that I took on the job.

After you screen the role & the CEO (and vice versa), you’ve built the foundation. From there it becomes a dance of understanding and then delivering business results.

As a Chief People Officer, you must be able to empathize with the CEO. You have to get them to be honest with themselves and with you about pain points in our organization, what’s working and what’s not. The empathy part is really key; you realize how hard it is to be a CEO, and how lonely it can be at times. You’re committing to becoming that person the CEO can talk to openly and honestly.

Finally, while empathy and understanding are critical, I also emphasize the importance of having a backbone and always standing up for what you believe in — CEOs respect CPOs who have a clearly defined thought process behind their actions (and especially their spending).

You have to get [your CEO] to be honest with themselves and with you about pain points in our organization, what’s working and what’s not. The empathy part is really key; you realize how hard it is to be a CEO, and how lonely it can be at times. You’re committing to becoming that person the CEO can talk to openly and honestly.

Circling back on getting to know your CEO — what questions do you like to ask your CEOs to really get to know them?

I like to learn about how they got to where they are, and what roadblocks they’ve faced along the way. I love hearing about their backgrounds and watching the way they carry themselves. For example, how do they think and talk about their family? It tells me a lot about how they’ll treat their people.

As for questions, there are no magic bullets, but here are a few I like:

  • Where did they grow up?
  • Where did they go to college, and why?
  • What was their first job?
  • Who do they go to for advice?
  • How did they choose their board members? How do they work with their board?
  • How did they select their current team?

Asking these seemingly simple questions about their background, their history, and their work, you start to get a sense of their value set really quickly.

Interested in reading the rest of this interview?

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Connor Swofford
Twine Labs

Growth @Twine, Founder @Paytronage (Acquired), Consultant @ATKearney, Graduate @Wharton