Leadership transition: How to best navigate with a remote workforce

Stash Chief People Officer Lynne Oldham explains the process behind choosing, announcing and onboarding new CEO

Leadership transition: How to best navigate with a remote workforce

From coast to coast, Lynne Oldham and Liza Landsman have been on the road meeting employees, fielding their questions and hyping them up for the future of the business.

It’s all part of Stash’s leadership transition strategy, as Landsman has recently been named new CEO of the New York City-based fintech firm. And, as chief people officer, Oldham has been instrumental in the process.

“You should have a point of view and opinion, and help the organization find that next leader who can take it to the next stage,” Oldham told HRD. “HR is in almost the best position of the C-suite to do that, given that we’re at the intersection of the people and the business.”

Even before Oldham, former chief people officer of Zoom, joined Stash last February, co-founder Brandon Krieg had been considering stepping down from the helm. He wisely included Oldham in the process (along with fellow co-founder Ed Robinson) from the get-go, even assuring her, “Don’t worry, we’re lockstep on this. We’re going to pick someone together.”

Finding a new CEO

The first step in the corporate recruiting process, Oldham says, was partnering with an agency familiar with the fintech industry and explaining “here are the attributes we’re looking for, here’s where we are as a company and what we’d like to see someone has done in the past.”

Then, the co-founders’ retinue – Oldham, the chief financial officer and some board members – began deep discussions as candidates were described. Stash’s decision-makers took it from there, testing candidates’ “been there, done that” skills, as well as their potential to be culturally additive.

“If you think about why you’ve seen some failures in leadership transitions, they’re mostly around culture and culture fit,” Oldham says. “You don’t have to fit into the culture exactly, but you have to be bringing more to the party. We were looking for someone who had joined a company at an inflection point for growth, but also someone who was interested in bringing forth our company’s mission.”

Landsman certainly had the enthusiasm and credentials Stash was looking for. With decades of experience in the finance industry, she has served in leadership roles at Citigroup, BlackRock and E*TRADE. She also led Jet.com from launch to its $3.3 billion acquisition by Wal-Mart, and most recently served as a General Partner at global venture capital firm NEA.

“Liza is the right person to lead Stash as we continue to hit major revenue and customer milestones and evolve the business,” Krieg said in a press release, alluding to Stash’s revenue surpassing $100 million and growing nearly 30% last year.

Don’t rush the onboarding process

Joining Stash’s Board of Directors in September 2022, Landsman was always intended to become CEO, but it wasn’t confirmed and public knowledge until this year.

“Creating excellent onboarding will get your new CEO in the right place to be successful quickly,” says Oldham, who has invested many hours breaking down organizational charts to Landsman.

The company took a two-pronged approach to announcing the decision to the workforce. First, leaders were able to meet Landsman and ask any questions before being given a FAQ document to address any employee concerns. One day later, the rest of the company learned of the new CEO at an all-hands meeting where they also were able to ask questions.

Oldham says transparency and clear communication are embedded into the organization, which holds an all-hands meeting every week where employees are kept abreast of what’s going on in the business. Another example of Stash maintaining engagement among its distributed workforce has been the monthlong road trip (culminating in London), in which Landsman has met 80% of employees in person.

“You can’t fly them all out to one city,” Oldham says. “I priced that out and it was massively expensive. You don’t want to spend a fortune on an all-hands jamboree, so we decided to go to them.”

Preparing a CEO’s exit strategy

Of course, there’s one other aspect of leadership transition that HR leaders need to navigate – offboarding the departing CEO. Well, in Stash’s case, Krieg is actually staying on board in the newly created role of head of business development.

“Because we’re privately held and our former CEO is a co-founder, he still has a lot of skin in the game and is really interested in making sure we’re successful,” Oldham says. “We talked about his skillset and how we can use that in a new world.”

“If a CEO isn’t staying around,” Oldham added, “I’ve done that, too. You make sure you have their brain dump somewhere so when they ride off into the sunset, we have that captured and part of the company’s fabric.”

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