Kara Wilson Oliver Explores Whether CHROs Have a Shelf Life—and What Advantages That Can Bring

Jason McRobbie

Welcome back to this week's P | A | C | T news, your bi-weekly newsletter by Tech Talent North.

This PACT dives into whether CHROs have a “shelf life” and why that might actually be a good thing. Kara Wilson Oliver (VP People & Operations, DealMaker) shares how adopting a builder-and-fixer mindset has shaped her career and highlights the power of product thinking in HR. Her journey reimagines the CHRO role as a mobile, high-impact career path with limitless potential.

Key takeaways:

  • With technologies alleviating the administrative side of HR, more focus is freed up for the profession to show its strategic value;
  • While core HR will always be needed, the value of bringing in a CHRO/CPO in the early phase of organizational development could be called immeasurable if it was not fully quantifiable; and
  • The perceived shelf life of the CHRO/CPO role is due to the fact that they are builders and fixers and moving between businesses every 18 months or so serves organizations well, while keeping their skillsets fully engaged.

Could there be a shelf life for those at the top of their game in the world of HR?

Having spent 25 years in the frenetic world of tech start-ups, Kara Wilson Oliver, VP, People and Operations with he capital-raising platform Dealmaker since November, works herself out of a job on a regular basis—and would not have it any other way.

Since bringing her product moxie to the people side of the equation, Kara’s mission to bring product methodologies into people practices has yielded success after success—albeit with a resume that she admits reads a bit like a roller coaster as late.

What Kara has discovered about herself and the CHRO role in the process is eye-opening and speaks to the evolving opportunities both within and beyond the profession.

Tabling the Concept of CHRO/CPO Shelf Life

While taking to the stage most recently at Tech Talent North to deliver a rousing speech to inspire HR to take bigger steps with a few tips from product design methodology, the conversation that has followed her since is one being grappled with by any number of HR pros at the top of their game in a start up scenario.

“Since I've moved over into people from product, I've had four of HR roles and all of them have been on average 18 months. The whole reason why I care about this is because using product methodology actually gets us into a different place in the organization, outside of classic HR, and I think it's one of the paths to making ourselves more relevant,” said Kara. “Ironically, at least in my particular case, it makes me relevant at a very narrow specific stage. When that stage is done—either because the org needs to get a lot bigger or a lot smaller—then I'm less needed. And it's time to spend my time building somewhere else. That’s been the big realization.”

Just the other week, Kara and 25 other CHRO/CPOs gathered for a round table discussion targeting that impermanency around the entire question of whether or not there is a shelf-life for their kind in an organization.

For Kara, co-leading the ‘yes’ table came naturally.

“I really am the most clear example of happily working myself out of a job every year and a half,” said Kara. “Each job was a bit different, but the pattern was the same. It was a bit of a rear view moment when I realized that this repeated pattern I was seeing actually kind of made sense in light of where we are at with the HR function.”

Kara points to the growing evolution of both the HR role, as well as the the technologies to support its original administrative task work.

“We continue to evolve the role and have a lot of smart people who have helped shed the administrative functions. We already have technology that supports our workflows, sets paths and processes for what to do for each employee to allow them to be self-sufficient, and AI only furthers that,” said Kara—with a caveat. “But as we continue to not only shed the administration, but actually accelerate and get out of that realm, we’re sort of left asking, ‘Okay, well, how do we bring value to the organization?’”

Answering that question has not only led Kara from green to lean pastures on more than one occasion. It has also grounded her belief that the answer to that quintessential question around HR’s raison d’être lies within how other functions operate.

HR Furthers Evolution in Footsteps of Other Functions

“My running theory and personal experience has been that answer lies in asking, What are the things that other functions in the organization do well—and how do we bring them into HR to continue to be useful and relevant?” said Kara. “Thinking about pipelines from a product perspective, thinking like a marketer, thinking like a salesperson—thinking about all this stuff that other functions already do, while HR sat in our castle surrounded by a moat. That has become less and less true though because our highest strategic value is now recognized as making sure we’re commercially responsible in the organization—and that’s a really, really vast mandate.”

So big that sometimes an organization needs to call a special teams unit to solve stage specific challenges, which is how Kara has come to understand her role in the big picture of small to mid-sized tech start ups.

“The base and ground level product problem solving is a muscle I use every day and most HR people are just beginning to explore, but I encourage everyone to adopt as a mindset. It’s getting in your reps around the financial stuff, the strategic framework and how the company actually operators and looking at your strategic goals using product language like P0 and P1 and zero problems,” said Kara, who recommends Built for People by Jessica Zwaan as a great guide.

“I’m a big fan of Jessica Zwaan and she speaks about this regularly. There’s a lot of opportunity in the Venn diagram of an early stage organization when you think about what a CPO versus COO can offer,” said Kara. “Adopting this mindset just brings you deeper into the roots and as commercially useful to the company as possible where your value is non-negotiable as a fixer and problem solver across any realm.”

What that work entails varies, but inevitably involves coming onboard, learning the company inside out and applying product management and process thinking to fix, solve and stabilize to desired result—then, in an inversion of the Peter Principle, moving on.

Meet the Special Forces of HR (Before They Move On)

“I'm a early-stage specialist. I’m not too interested in the initial start up phase as I need to have the initial product market fit, so not stage A, but an early stage B,” said Kara. “What I'm doing is making sure that the team that I have is lean, but also very commercially relevant to the outcomes of the organization. Once the initial build is done, I will leave a team in place to operate it. So my theory is that there's an age and stage of companies that I am a specialized for. ”

What Kara has discovered in her conversations with other CPOs is that this actually might work well for everyone involved.

“What has come up time and again with other Chief People Officers is that once you have built a thing, you can plateau, right? What we discovered was that moving to another company was incredibly liberating, almost like swapping jobs between two companies,” said Kara. “What we realized was that it was actually a lot like a change of CEO—something needed to keep things not just fresh, but actually allow you to continue to problem solve and apply novel first principles thinking.”

“Otherwise you're like, ‘Okay, let me look at the benefits again and let me look at the same problem set of the same employee base again,” she added. “But my theory is that you actually need to move in order to apply that novel problem solving.”

The Difference Experience Makes to a Unicorn

That value can actually be measured in unicorns, Kara notes, pointing to a study by Maddy Cross, former Talent Director at Notion.

“Maddy did a longitude study looking specifically at startups that eventually became unicorns. Interestingly, the things that did not determine whether or not they were going to become a unicorn was how much they raised,” said Kara.

The number one thing that did matter, Kara notes, speaks directly to the shelf life at the heart of our conversation.

“The number one thing that did really matter was stage recognition. With unicorns, the people that they brought in as stage experts only stayed for about two years. It turns out the average tenure of unicorn executives is below two years,” said Kara. “I think about it like a movie. I’m the pilot season. I'm not season six. It's a totally different energy.”

Thinking of CHROs and CPOs in that light—as stage experts, special forces—recasts the question of career shelf life in a new light of opportunity, Kara notes.

It also opens the HR career path to previously unconsidered opportunity.

The Profits of the Mobile Career

“It's possible that I'll continue to move around and and hop into a new organization as a fixer every 18 months, do my thing, deploy the product management toolkit—and then move to a new place where it will be a completely different relationship and set of challenges,” said Kara, while leaving room for further evolution beyond HR where her combined product and people prowess might have even greater impact.

“Coming from product, I would eventually like to be an operator, so my path is product, people, operator and I envisioned the people part to be five to 10 years and I am in the fourth year of that journey,” said Kara, having fully embraced the mobility of role and overarching goal. “It’s all about building a repertoire to be a useful operator.”

That said, ongoing change and evolution is something that Kara both embraces and encourages within the profession, she has also come to learn what she will not change regardless of role or title.

“I won’t change the stage of the company. I love the energy. I want to be in the trenches. I'm not a consultant. I want to be the builder. I want to make my case in the big, messy, 50 to 200 person stage companies, where everything breaks and, everything feels chaotic and it’s all two steps backward and one step forward,” said Kara. “Because then I can pull so much from the toolkit, not just bring stability to the HR function, but broadening the people function and applying it into leadership.”

In that thinking, Kara lays a path forward that points to the future of the HR function, as well whatever happens next on her own CHRO/CPO journey—because while their may be a shelf life, there is clearly no expiry.



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