Matt MacInnis

President and head of product at Rippling

Matt MacInnis is President and Chief Product Officer of Rippling, the workforce-management company that unifies HR, IT, finance and payroll on one system of employee data. Rippling's leadership page lists him next to co-founder and CEO Parker Conrad, and the company says its software connects with more than 600 other applications and that it works from ten offices across four continents.^[1]

Rippling's own biography says he oversees the product organization, and a 2025 conference speaker profile adds that he is responsible for developing the company's HCM, payroll, IT and spend suites. The same leadership page quotes him explaining that Rippling built one global system for finance, HR and IT because the company understands what is happening under the hood for its customers.^[1][2][6]

A title that has changed over time

MacInnis has held more than one senior title at Rippling. In a June 2020 interview on the Second in Command podcast he was Rippling's chief operating officer, with formal responsibility for areas including HR, finance, business development, product design, and customer support and success. As of a November 2024 podcast episode he was still introduced as COO.^[3][4]

By 2025 a conference profile listed him as Chief Product Officer, and Rippling's current leadership page lists him as President and Chief Product Officer.^[1][6]

Apple years

Before founding a company of his own, MacInnis spent about eight years at Apple, where Rippling's biography says he worked on growing the use of Apple products in education and the sciences. He holds an electrical and computer engineering degree from Harvard, according to the same biography, and lives in San Francisco.^[2][3]

Founding and leading Inkling

MacInnis co-founded Inkling in August 2009 with Josh Forman and Robert Cromwell and served as its chief executive. Wikipedia's history of the company records an iPad app launch in August 2010, publishing partnerships with Wiley, McGraw-Hill and Wolters Kluwer, and a shift in early 2014 from selling to consumers toward selling to businesses. By 2016 it had raised a reported 95 million dollars; Rippling's biography puts the total above 100 million dollars.^[2][5]

Rippling's biography describes Inkling as a mobile learning platform acquired in 2018, and the 2020 interview describes it as a mobile on-the-job training platform he co-led from 2009 to 2018. Wikipedia separately records Echo360 acquiring Inkling in May 2024.^[2][3][5]

In that 2020 conversation he said that although Inkling was built to profitability, the outcome returned only a fraction of the capital invested, which he said took away any sense of being a predestined success. He took from it the lessons that effort does not guarantee results and that, in his words as summarized by the interviewer's notes, life is a team sport.^[3]

Joining Rippling

MacInnis told the Second in Command podcast that he already knew Parker Conrad well and had invested in Rippling's seed round before joining as an executive. He gave three reasons for joining: the chance to build a company with a close friend, skills that complemented Conrad's, and conviction in the market-share flywheel he saw in the business.^[3]

He said he was won over after Conrad pushed back on an early critical email he had written, and that he was drawn to the data architecture, which had been designed from the start to work as a database for other systems. Rippling's product logic rests on that design: integrations such as a spending limit on a partner card that updates when an employee's role changes inside Rippling.^[3]

How he operates and leads

In the 2020 interview MacInnis described himself as subordinate to the CEO on final decisions but a copilot who acts with real autonomy. He said he treats the management team as peers, gives feedback regardless of reporting lines, and will debate Conrad in front of the team to surface concerns others hesitate to raise, while deferring to him in front of the board and handling disagreement privately.^[3]

On process, he said he builds it from how people actually work and adds it only once its absence causes real pain, and that Rippling plans quarterly. On hiring, he said he hires only when a need becomes pressing and is wary of search firms that push for fast decisions. He keeps a running agenda for each direct report and maintains a user manual describing how to work with him.^[3]

His November 2024 appearance on the Grit podcast was built around one argument: a non-founder executive's first job is to learn the engine of the company they join, and the executive team should support the CEO's strengths and cover the rest. Topics listed for the episode include working with about 150 former founders at Rippling, a meeting with Steve Jobs, disagreeing with Conrad, and the collapse of Silicon Valley Bank.^[4]

Why he matters

Rippling is a compound-product company, selling many integrated modules rather than a single tool, and that strategy depends on a product and operations leadership able to ship across HR, IT, finance and spend at once. MacInnis is the executive who has held both ends of that job, first running the business and now the product organization, which makes him one of the central figures in how Rippling turns its single employee data model into products.^[1][2][6]

On The Executive List

Matt MacInnis is ranked No. 17 on The Executive List (October 2026) in the Chief Operating Officers discipline. The Executive List edition records him as Chief Operating Officer; Rippling's leadership page now lists him as President and Chief Product Officer. The ranking reflects The Executive Review's own editorial Trending Score; it is not an outside award, and placement on the list is never sold. View the October 2026 edition.