Topline · 17 Sep 2026 · From the week of 14 September
SPOTLIGHT: What It Takes to Step into the CEO Role | Eric Anderson, CEO @ Walnut
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Eric Anderson, CEO of Walnut, describes his first six months as a first-time CEO, taking over a founder-built company with a global team split between Israel and the US. He previously ran go-to-market teams as president or CRO, and AJ Bruno hosts, sharing his own founder and board experience. The episode covers his listening tour, the Tel Aviv executive offsite, board management, and tough decisions on pricing, segmentation and unprofitable markets. The central argument is that a new CEO should keep what works in a founder's business, change what is clearly broken, and recognise that serving both enterprise and SMB customers is very hard.
For founders
- Stepping into a founder-built company means inheriting the founder's culture, vision and equity, so the job is to keep what works and change what is clearly broken.
- If you want to attack enterprise, question whether you should also sell to SMB, because the two need different product strategies and go-to-market approaches.
- Spend the first 30 days on one-on-ones with everyone in the company to find out where the problems are.
- Stopping work in markets you know are unprofitable is hard and scary, but Eric Anderson's experience at Walnut was that the team kept chasing them for too long.
For revenue leaders
- When the product is strong, the biggest opportunities can sit in marketing, sales, customer success and how the company presents itself to the market.
- Bringing in experienced executives with fresh eyes to rebuild go-to-market leadership has, according to Eric Anderson, breathed new life into Walnut.
- Calling enterprise customers you have sold to before and asking about the tech, support and experience is a direct way to check how the product is perceived.
- Pricing that had gone unchanged for several years at Walnut was a decision the company could not get past, and an overhaul is now underway alongside segmentation changes.
What was said 19, most useful first
If you want to attack enterprise, question whether you should also sell to SMB, because they need different product strategies and go-to-market approaches. Listen
Eric Anderson says trying to serve everyone well is an impossible task, because it is hard to build one product that suits everybody's needs. He describes enterprise and SMB as needing two different product strategies and two different go-to-market approaches, which he compares to two different companies.
“if you really want to attack the enterprise, you should really question whether you're trying to sell the SMB at the same time because those are two different product strategies and two different uh you know ways to go to market entirely, different companies.”
Stepping into a founder-built company is not like replacing another CEO, because you inherit the founder's culture, vision and the equity they put in. Listen
Eric Anderson, a first-time CEO taking over Walnut from its founder, says the culture, vision, mission and sweat, blood and equity the founder poured in all come with the role. He says you step into it for both the good and the challenges that need to be fixed.
“It's not replacing just another CEO. You're stepping into something that he created.”
A new CEO of a founder-led business should keep what is working and change what is clearly broken. Listen
AJ Bruno says the incoming CEO's job, as steward of something that already exists, is to highlight and embrace the parts of the business that are working while changing the parts that are clearly broken. Eric Anderson agrees, adding that pointing out what is not optimized has to be done in a way that unites the team rather than separating people.
“how do we make sure we highlight and embrace the parts that are working, but we change the parts that are clearly broken”
Some leaders are tied to the belief that what got them to their current stage will get them to the next one. Listen
Eric Anderson says some people are very attached to this belief, whether the target is 20 million or 30 million in ARR and beyond. He says a new leader's fresh eyes can point out areas that are not optimized, and doing so is a delicate balance against pulling teams together.
“some people are very tied to believing that what got them there is going to get them to the next stage whether it's to 20 million or 30 million in ARR and beyond.”
A new CEO can learn where the problems are by spending the first 30 days on one-on-ones with every person in the company. Listen
Eric Anderson spent his first 30 days after joining Walnut on a listening tour, meeting every person in the company one-on-one. He was trying to get each person's view on where they thought the bones were buried and what the challenges were.
“I spent 30 days after joining just doing a listening tour and just getting to know every single person in the company and doing one-on-ones and trying to get everyone's perspective on where they thought the bones were buried and some of the challenges were.”
A new CEO brought the executive team to Tel Aviv for an offsite to let them learn his tone and pace and to unify a previously siloed leadership team. Listen
In January, Eric Anderson took the executive leadership team to Tel Aviv for an offsite. He used it so the team could get to know him and understand the tone and pace he wanted, and to pull together a leadership team he described as having been very siloed.
“then in January I took everyone to Tel Aviv, the executive leadership team to Tel Aviv when we did an executive offsite.”
Setting one operating plan and four big annual OKR objectives was how a new CEO aligned the executive team. Listen
After the Tel Aviv offsite, Eric Anderson's team set an operating plan and OKRs with four big objectives for the year. He used these to align the entire executive leadership team, and called this the first big challenge handled.
“So we set an operating plan, we set OKRs, four big objectives for the year. Um and really use that as to align the entire executive leadership team.”
Strong opinions loosely held across an organization led to people vacillating, either stuck in data paralysis or unable to make progress on the areas they felt strongly about. Listen
Eric Anderson says indecision was where Walnut struggled most, with teams swinging between positions and either getting sucked into analysis for too long or getting nowhere on their strong views. He describes this as the root of the stalled pricing and unprofitable-market decisions.
“I like to say uh strong opinions loosely held across the organization uh and uh they would vacillate and and either get sucked into data, you know, paralysis for too long.”
Pricing that had needed updating for several years was a decision the company could not get past. Listen
Eric Anderson says Walnut's pricing had needed to be updated for several years and the company had not been able to move on it. He now describes a pricing overhaul, alongside work on market segmentation and on which market to focus on, as one of the initiatives for the year.
“pricing had needed to be updated for several years and they couldn't get past it.”
Continuing to chase markets the company knew were unprofitable, because stopping felt scary and hard, was a pattern at Walnut. Listen
Eric Anderson says Walnut kept going after markets it knew were unprofitable because the decision to stop was scary and hard. He adds that people tend to focus on the negative impact of such a change rather than the positive outcomes it would bring.
“markets that they knew were unprofitable that they were continuing to chase after they would just continue to keep doing it because the decision to not do that was scary and it was hard”
A CEO can check how the product is perceived by calling enterprise customers they sold to before and asking about the tech, support and experience. Listen
Before taking the role, Eric Anderson, who had sold to several of Walnut's large enterprise customers, called them to ask what they thought of the tech, the support and the experience. He reports that the product was rock solid from their standpoint, which pointed him to go-to-market as where the challenges lay.
“so I blindly called into these companies and said hey what do you think and uh you know how's how's the tech and how's the support and how's the experience been uh and as I suspected that it's it's solid, rock solid from that standpoint.”
Listen to the episode Retention & customer success Link to this
When the product is strong, the biggest opportunities can sit in go-to-market teams, including marketing, sales, customer success and how the company presents itself to the market. Listen
Eric Anderson found Walnut's product and engineering solid, so the challenges to turn into opportunities were in the strength of the marketing engine, the sales organization, the success teams and how the company presented itself. He said this left a lot of room to improve.
“a lot of the opportunity or the the challenges to become opportunities really existed in the strength of the go to market teams uh the marketing engine, the sales organization, the success teams uh and how we present ourselves to the market.”
Bringing in experienced executives with fresh eyes to rebuild go-to-market leadership has breathed new life into the company. Listen
Eric Anderson hired a new head of marketing in January and recently a new head of customer success. He says these experienced executives have helped breathe new life into the company, and that other team members are now seeing progress and success in market.
“So uh refortifying some of these organizations uh with exe experienced executives with fresh eyes um has really helped breathe new life into the company.”
Cutting a micro-SMB segment after moving up market was hard, because the CEO has to deliver the bad news and the decision can feel like a failure. Listen
AJ Bruno describes a micro-SMB segment at his company that they decided to cut as they moved from SMB toward mid-market. He says the CEO has to own the bad news, and that the decision can feel like a slight against the people who made earlier choices, which makes it hard to move forward.
“we had a segment was like micro SMB. We're like, we just have to cut this part of the business, but we got to rip the band-aid off and deliver the bad news.”
A new CEO has to balance giving the board enough oversight and visibility without educating them as if they were another founder. Listen
Eric Anderson says being responsible for the board is different from participating in it, even after raising institutional funding and attending many board meetings. He describes a balance between giving the board the oversight and visibility they want and not being so open that you feel you have to educate them as if they were founders.
“not completely open and transparent where you feel like you have to educate them as as if they were another founder.”
AJ Bruno keeps board meetings quarterly, moving to monthly when things are going less well, and has never had them weekly. Listen
AJ Bruno says he has had more than 70 board meetings over the years and tries to keep them quarterly. He says they sometimes become monthly when things are not going as well, and that he knows CEOs who have had weekly board meetings.
“I try to keep them quarterly and sometimes when things aren't going as well, they they become monthly. I've never had them go weekly”
After a CEO change, a business can become indecisive, with leaders reluctant to rock the boat on choices such as brand and positioning. Listen
AJ Bruno says his company showed some indecisiveness after a CEO switch, especially with founders still involved, with the team reluctant to rock the boat. He gave brand choices and positioning as examples and said there is a ramp period to get through.
“there was some level of indecisiveness when we had a CEO switch just like not rocking the boat.”
The CEO has no one else to turn to for shaping board messaging and narrative, so that work falls entirely on them. Listen
Eric Anderson says the CEO role is the loneliest job in the world. He says there is no other person to help position a board meeting, build the messaging or create the narrative, and that all of this sits with the CEO.
“there's no other person you turn to that's going to help you with, yeah, how do we position this board meeting and how do we build the messaging and how do we create the narrative? That's all in you now.”
Sending a six-question pre-read on The Advantage before a management offsite is a way to test how aligned the team is. Listen
AJ Bruno says his team read Patrick Lencioni's The Advantage and worked through six questions before their management offsite. He says the answers will show how aligned or misaligned the team is when they meet.
“So we did like a pre-read, six questions, and I'm excited to see how aligned or misaligned we are headed into next week.”