[Un]Churned · 28 Jan 2026 · From the week of 26 January
This CCO Won't Ask His Team What He Wouldn't Do Himself (And Why) ft. Jim Richmond (Smartling)
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Jim Richmond, Chief Customer Officer at Smartling, an AI-powered translation and localization company in business since 2009, speaks with host Josh Schachter, SVP of Strategy and Market Development at Gainsight. The episode covers his FY2026 priorities, including gross revenue retention as the North Star metric, his four-quarter forecasting process, role specialization for CSMs in the AI era, a support bot that changed ticket patterns, and his time allocation and career advice. The central argument is that a leader should not ask the team to do what they wouldn't do themselves, and that systems and specialization are needed to grow without doubling headcount.
For founders
- Smartling's second priority is operational leverage, growing the business without doubling, tripling or quadrupling headcount, through systems and processes.
- Richmond says to build systems for the size the company will reach, because the team is as small now as it will ever be.
- At enterprise stage, Smartling splits customer success into onboarding, technical and value roles, which Richmond sees as the only real route to operational leverage.
- Richmond predicts the big AI winners over the next few years will be AI application companies rather than companies building their own tools.
- Richmond argues predictable forecasting builds board trust, which he links to good financial metrics as the company grows.
For revenue leaders
- Smartling's FY2026 North Star is gross revenue retention, with the aim of keeping retention as close to 100% as possible.
- Renewal forecasts start broad from CSM judgment and tighten quarter over quarter as renewals approach, and Richmond expects early numbers to run low because people want to look like heroes rather than goats.
- A bot placed in front of Smartling's support workflow removed single-touch tickets, so multi-touch tickets rose sharply and the support team still needs to grow.
- Richmond aims to split his CCO time into thirds across customer interactions, administration, and recruiting and growth, though he says administration currently runs higher.
- Richmond keeps his own book of business and works support tickets so that he models what he asks of his team.
What was said 19, most useful first
Renewal forecasts start broad with CSM judgment and tighten each quarter as renewals get closer. Listen
Richmond said the forecast begins with the book that needs renewing in a fiscal period, and individual contributors give their best call, such as retaining 100% of revenue or treating it as a coin toss. Each quarter the forecast is refined by asking customers about their plans, capacity and word volumes for next year, until it approaches dollars and cents.
“it starts out being a pretty broad strokes of just what is the book that we need to renew in a given fiscal period”
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Early forecasts tend to run low because people sandbag so they look like heroes rather than goats. Listen
Richmond said people will call a number lower than they really think to avoid a bad surprise, and he said he is the same way. He expects Smartling's GRR number to rise as that bad-surprise effect is removed and the forecast gets close to what the company will actually deliver.
“they'll call a number that's lower than what they really think because they want to look like a hero rather than a goat”
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Enterprise-stage customer success gets operational leverage by splitting CSM work into onboarding, technical and value roles rather than generalists. Listen
Richmond said he does not want CSMs to be generalists and wants them to be excellent at what directly affects core metrics. Smartling's model has an onboarding team focused on getting customers to value quickly, a tech team that knows the platform and resolves issues, and a value team focused on commercials, renewals and economic buyers.
“the only real way to get operational leverage is is to specialize those roles.”
Listen to the episode Retention & customer success Link to this Report a problem
Richmond predicts the big AI winners over the next few years will be application companies, not businesses building their own tools. Listen
He argued that a company building a highly specialized piece of software with general AI tools will not get something better, cheaper or easier to maintain than an off-the-shelf product, because the risk and benefit are not in line. He expects specialized AI applications to win in customer success and support, where problems are smaller, tightly controlled and have data to train models.
“a lot of the big winners that are going to be out there over the next few years are going to be AI application companies”
An LLM bot placed in front of Smartling's support workflow removed single-touch tickets, leaving more complex multi-touch tickets. Listen
Richmond said customers, especially technical users, often wanted to talk to the bot first, and adoption was strong even though use was not mandatory. The bot handled simple how-do-I and where-is questions, so multi-touch tickets rose sharply. He said Smartling still needs support professionals, more than ever, and plans to keep growing that team.
“the bot has completely removed all the, all the single touch tickets.”
Listen to the episode Retention & customer success Link to this Report a problem
Richmond keeps his own book of business as CCO because he is unwilling to ask his team to do what he wouldn't do. Listen
He said he models behaviour for the whole organization by holding sit-downs with the support team, working tickets, and carrying his own book of business and GRR number. He said he wants to be able to say he has his own book and his own GRR number, and that it either works or doesn't.
“for me as a leader, I am unwilling to ask someone to do something that I couldn't or wouldn't do myself.”
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Smartling set gross revenue retention as its North Star metric for FY2026, with net recurring revenue treated as secondary. Listen
Jim Richmond said the focus is protecting the existing book of business so the company has a solid foundation for growth. He said the company has to retain customers at as close to 100% as possible, while still generating leads for sales partners.
“That's, that's our new North Star metric for, for the year.”
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Operational leverage is the second priority, so growth should not require headcount to double. Listen
Richmond said Smartling does not want to double, triple or quadruple headcount as the business grows. He said the goal is to make people in their seats more efficient and effective through systems and processes, and he described this as the second big rock behind GRR.
“We don't necessarily want to double and triple and quadruple our headcount, right?”
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Smartling runs a four-quarter forecast with a target for every quarter over the coming year. Listen
Richmond wants a target for each quarter so he can spot challenges far enough out to fix them or build buffer against surprises. He drew on his time as VP of customer success at Sprinkler, where fast growth made it hard to know what GRR would be in any quarter.
“to identify that those challenges far enough out that I still have time to, to fix them”
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Build systems for the scale the company will reach, since the team is as small now as it will ever be. Listen
Richmond tells his team on staff calls that the current team is the smallest it will ever be, so systems that would not work at several times the size should be built now. Dashboards give him the numbers for his board deck and give individual contributors their likely bonus and the accounts they need to win.
“This is the smallest this team will ever be.”
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Small scrappy companies need CSMs who do everything, but enterprise-stage operations require specialization. Listen
Richmond described a CSM at a small company doing an annual business review, then a deep technical troubleshooting call, then an onboarding conversation, because people are still proving themselves in the market. He said that as Smartling moved to an enterprise localization play, that model had to give way to specialized roles.
“you got to be willing to do everything right.”
Listen to the episode Retention & customer success Link to this Report a problem
Josh Schachter expects CSMs to become more generalized, with depth coming from a toolkit of specialized AI tools. Listen
Schachter said he expects many specialized applications, such as onboarding software, but thinks the CSM role will widen end to end, with the depth of each CSM coming from how they use the full set of specialized AI tools. Richmond responded that one person will be able to do a lot more with copilot-style AI.
“I actually think that the CSM is going to become a little bit more generalized.”
Richmond wants AI-enabled CSMs to cover more accounts efficiently rather than broaden their scope. Listen
Richmond said he agreed that copilot-style applications give one person much broader depth of knowledge. From an operational leverage standpoint, his aim is efficiency, meaning people can cover many more accounts because they have a clear picture of what they need to do and tools to do it very efficiently.
“I want, I want people to be able to to, to cover a lot more accounts because they've got a very clear picture of exactly what they need to do”
Richmond aims to split his CCO time into thirds across customer interactions, administration, and recruiting and growth. Listen
He said he tries to spend a third of his time with customers, a third on administration and a third on recruiting and growth, though he says he is not terribly successful and the balance is lumpy from week to week because of customer trips. Administration is currently higher than he wants because of tool investments, process changes and rethinking how teams measure success.
“I try to spend a third of my time in customer interactions and a third of my time in doing administration right”
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Seeking varied experience across sales, CS, solutions and services builds the empathy that makes a leader a more authentic partner. Listen
Richmond's career included selling, leading sellers and owning a forecast, working as a technical account manager, leading success teams, solutions consulting and professional services. He said this makes it easier to understand what colleagues care about, and he pointed to the difficulty of making cold calls and being rejected, which gives him empathy for sales partners.
“I know how hard it is to make 10,000 cold calls and, and get hung up on 9999 times, right?”
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Leaders should make individual contributors feel they belong, are respected, can grow and are understood, and connect their daily work to company results. Listen
Richmond said that over 20 years as a leader, cultivating this has been one of the most important things he has done. He meets people where they are and shows how day-to-day work adds up to the company's accomplishments, which he said gives people a sense of reward and purpose beyond a paycheck.
“it's critically important that people feel like they belong, that they're respected, that they have room to grow and that and that they're understood.”
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Poor forecasting produces surprises, and predictability builds the board trust that leads to good financial metrics. Listen
Richmond said the impact of poor forecasting is surprises, and that boards want leaders to do what they say they will do. He said predictability leads to stability and trust. He also said a solid command of the business lets leaders allocate resources effectively, which he called the job of a leader.
“The impact of poor forecasting is surprises.”
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Smartling's customer engagement organization is about 50 people across support, professional services, managed services and customer success. Listen
Richmond said the customer engagement organization he leads has about 50 professionals spread across the United States, Latin America and Europe. He said the company has several hundred employees and revenue in the hundreds of millions of dollars, and that the company is remote first.
“The customer engagement organization that that I support is a team of about 50 professionals”
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As Smartling's first CCO, Richmond can optimize the customer journey across functions with a cross-silo view. Listen
Richmond said this is the first time Smartling has had a CCO, and the role lets him optimize the customer journey across several functions with the customer's experience as the north star. He said in smaller roles the work was more about influence, while this role gives him a broad cross-silo perspective.
“I get to optimize the customer journey across a bunch of different functions”
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