Tresidder runs a company built around a small, unsexy claim: most one-on-one meetings between managers and their reports don't happen, and when they do, they aren't very good. Leadr, the software he co-founded in 2019 and has run as chief executive since February 2021, exists to schedule those meetings, prepare their agendas, capture the notes, follow up on the goals, and, when possible, turn them into something a human being might describe as coaching. This is either a boring premise for a Series A company or the single largest overlooked market in enterprise software, depending on which of Leadr's 500-plus customers you ask.
The company sits in the awkward, correct space between HR software and productivity software. HR software watches you. Productivity software organizes you. Leadr, which sells to somewhere around 10,000 active users, tries to develop you, which is the harder verb. The pitch is that if a manager runs a decent one-on-one every week and links it to goals and feedback and a personal development plan, then, eventually, you have a company where 130 people work more like the one person Tresidder remembers from Pushpay.
§ 01 · The InsightThe one out of 130
The Pushpay chapter is short and it is the whole story. Tresidder was 29. He was VP of Sales for a New Zealand-born church-technology company that would eventually go public, cross $100 million in revenue, and serve more than 7,000 customers. He had 130 people reporting up into him. One of them, he says, did the thing everyone in the middle of the org chart is supposed to do and mostly doesn't: showed up with a will to improve, a connection to the mission, and empathy for the customer.
He wanted, he told everyone who would listen, 50 more like her. He could not consistently produce them. The 90 percent he could never seem to reach, in his phrasing, became the addressable market. Leadr is the company built to reach them, or at least to give their managers a fighting chance of doing it themselves.
The 90% I could never seem to reach consistently.
— Matt Tresidder, on the insight that seeded Leadr§ 02 · The Phone CallHeaslip, from overseas
The origin of Leadr, in the retelling, is a phone call. Chris Heaslip, the co-founder of Pushpay and now Leadr's executive chairman, called Tresidder while Tresidder was traveling internationally. Heaslip had an idea about people development software. Tresidder said yes. The company was incorporated in August 2018 and launched from a small office in Redmond, Washington in spring 2019, with five employees on the payroll. The public platform launched in May 2020, one of the least favorable months in recent memory to launch anything, and the headquarters moved to Plano, Texas in February 2020, one of the most favorable years in recent memory to leave the Pacific Northwest for the Sun Belt.
Tresidder was Chief Revenue Officer for two years, which is a title co-founders give themselves when they don't want to be CEO yet. He became CEO in February 2021. Heaslip, on the way out of the CEO seat, offered the following endorsement: "Matt is one of the finest executives I've worked with." Five months later, in July 2021, Leadr closed a $10 million Series A led by Bedrock, with participation from Heaslip, Intuit's CRO Bobby Morrison, and Pushpay co-founder Eliot Crowther. Total funding is roughly $14.66 million. The checkbook, in other words, is largely made up of people who watched Tresidder run sales for Pushpay and drew a straight line.
§ 03 · The CurriculumAuckland → altMBA → Wharton
Tresidder's formal education is worth reading closely because it doesn't include a bachelor's degree in the ordinary place a bachelor's degree would go. He studied at Life Leadership College in Auckland, graduated from Seth Godin's altMBA, and completed the Wharton Business School's executive program in Finance and Accounting. That is a resume that reads like it was assembled à la carte by somebody who cared more about the reading list than the diploma, which is more or less how Tresidder has described it in podcast appearances.
The Godin connection matters. altMBA graduates tend to talk in Godin cadence - short sentences, kind provocations, the odd manifesto - and Tresidder is no exception. His personal site opens with three words: Leadership can be learned. It is the sort of statement that sounds obvious until you notice that most leadership software is built on the opposite assumption.
Leadr Growth
Rough milestones since incorporation
§ 04 · The ThesisManagement, dead
Tresidder and his co-founders wrote a book with a title that is, at minimum, an act of positioning: Management is Dead. Coaching, in their reading, is what comes next, and it is what the software is for. Leadr's platform stitches together the weekly one-on-one, the personal development plan, the feedback loop, the goal, and, more recently, the Patrick Lencioni curriculum that came with a partnership with The Table Group. There is an AI notetaker, because there is an AI notetaker in every product now, and there is a Leadr Academy layer, which teaches the manager on the other end of the software how to actually use it.
The two-word framework Tresidder returns to in interviews is care versus candor. Too much care and there is no growth. Too much candor and there is no trust. A functional manager, in the Tresidder model, holds both at once and the software makes it slightly harder to skip either.
Leadership can be learned.
— The whole homepage, essentially§ 05 · The LifeKiasa, Lucy, and Addison
Tresidder lives outside Dallas with his wife Kiasa and a dog named Lucy. The company is now headquartered in Addison, Texas, a suburb best known for its skyline of chain restaurants and an annual air show. Leadr has been named a Dallas Best Place to Work three years running in the "Best at Values" category, which is either a tautology given the product or a proof point given the product, again depending on which of the 100-plus employees you ask.
The New Zealand accent has softened. The company has scaled from five in Redmond to something like ten times that. The Pushpay diaspora - Kiwis who came to America to sell church tech and stayed - continues to reshape a corner of American SaaS most people don't notice. Tresidder is currently the most visible member of that diaspora who isn't already in the church-technology aisle.
§ 06 · The NumberOne million
The number Leadr repeats, the one on the website and in the pitch, is one million. That is how many leaders the company wants to develop through its software. It is a round number and a large one. It is the sort of target that in another industry would be treated as marketing, and in this industry is treated, mostly, as marketing. Whether Tresidder gets there is not obvious. What is obvious is that if you spend an hour with him and let him talk about the one employee out of 130 who had the will and the mission and the empathy, he will circle back to the same idea from a slightly different angle every twelve minutes until the meeting ends. That is either the discipline of a founder who has found the through-line of his company, or a very specific form of Kiwi patience. Probably both.
Tresidder is 30-something, running a Series A company in a suburb of Dallas, married to Kiasa, walking Lucy, holding a very specific opinion about one-on-one meetings. He is trying to raise the floor on middle management by roughly one million people. The software either helps or it doesn't. He seems willing to spend a decade finding out.