28. Do product leaders make good COOs?

In this episode we discuss being COOs with former product leaders Martyn Fagg, COO of Tillo and Matt Jones COO at ex-COO at ParentPay.


2/1/20245 min read

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Bethany and Brandon discuss the following:

  • What does a good product leader look like?

  • What does a good product manager look like?

We then discuss the following with Martyn and Matt:

  • How did the transition to COO happen?

  • Was picking up the people function challenging?

  • How do you get the people function to be more data-driven?

  • How do you get product development and commercial to learn from each other?

  • What product development KPI should be included in the company dashboard?



Martyn Fagg is a seasoned CTO with 20 years experience in software engineering and fintech leadership - passionate about fostering innovation, collaboration, and continuous learning. Currently COO at Tillo, a B2B embedded rewards & incentives platform working with some of the world’s top brands to deliver real-time digital gift & prepaid cards.

Matt Jones recently served as the Group Chief Operating Officer at ParentPay, a leading provider of payments and MIS solutions for schools in the UK and Europe. He joined the company in 2017 and initially held responsibility for Product Management, Software Engineering, IT, Service Operations, Customer Implementation, and Customer Support across several early Group businesses (ParentPay, Schoolcomms, Cypad, WIS, and nimbl). Additionally, Matt oversaw the group Security function, ensuring the protection of the company's and customers' data assets.

Prior to his tenure at ParentPay, Matt briefly served as COO at IRIS Software. He also spent six years as Senior Vice President of DevOps at NewVoiceMedia (acquired by Vonage) and held previous roles at Mimecast and MessageLabs (acquired by Symantec).

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  • Product development in CEO role with Twilio and Parent Pay leaders. 0:06

    • Brandon and Bethany discuss their cultural heritage for a school event, with Brandon dressing as a tech bro from Silicon Valley and Bethany dressing as a Canadian with a hockey jersey and maple syrup.

    • The hosts joke about stereotypes and cultural representations, with Brandon accidentally saying "boot" instead of "boot" and Bethany pointing it out.

    • Brandon M. questions the importance of good product leadership, emphasizing the need for a clear product vision and strategy, as well as effective team building.

    • Martin Fag, Matt Jones, and Brandon M. discuss the role of product development in the CEO role, with a focus on product leadership, strategy, and team building.

  • Product leadership and CEO roles in tech companies. 4:50

    • The CEO and product leader roles require different skills and perspectives, with the CEO focusing on the overall vision and strategy, and the product leader translating that vision into a tangible product.

    • The product leader must be empowered to take ownership of the vision and make it a reality, while the CEO can evolve their role to focus on other aspects of the business.

    • CEO and product leader have different visions for product strategy, leading to potential conflicts.

  • Product management and leadership. 8:51

    • Brandon M highlights the importance of product managers understanding users, market dynamics, and stakeholder management to ensure a product's success.

    • Bethany agrees, noting that product managers often focus too much on technical details and not enough on validating with customers and stakeholders.

    • Brandon M discusses Marty Kagan's philosophy of product development, emphasizing the importance of empowered teams with autonomy, resources, and scope to solve problem areas.

    • Bethany agrees and adds that being given a problem to solve, rather than features to build, is crucial for product development teams to make a difference.

  • Product management and CEO roles. 13:39

    • Bethany and Brandon discuss the role of a good product person and CEO, with Bethany highlighting the importance of being able to pull oneself up and out of the weeds.

    • Martin fell into the role of CEO as an opportunity after growing the company from six to 50 people and wanting a new challenge.

  • Career progression from CTO to CEO. 16:12

    • Matt Jones describes adaptability and willingness to take on new roles as key to his success as CEO.

  • Leadership roles and responsibilities. 17:38

    • Bethany shares her experience of being the only woman in a male-dominated leadership team and feeling like she's often overlooked or undervalued.

  • Leadership roles and responsibilities. 18:56

    • Martin, a former software developer and CTO, now CRO, has been managing people for 15 years and enjoys the people side of things, working closely with Briney, VP of people.

    • Martin took on the people function as CRO, bringing a unique perspective as he has the largest proportion of the company reporting into him, and he works closely with the executive team to bring a commercial and business perspective.

  • Managing people and teams in a cross-functional environment. 21:53

    • Matt Jones highlights the importance of managing people as individuals, not just roles, in a cross-functional organization.

  • Using data to inform people policies in a business setting. 23:18

    • Matt Jones and Bethany discuss the importance of data in people policies, with Matt agreeing that data can provide insights into people's performance and wellbeing, while Bethany struggles with getting people teams to own and use accurate data.

    • Both Matt and Bethany agree that there needs to be a clear owner of people data, such as a business ops team, to ensure accuracy and better decision-making.

  • Data governance, culture, and retrospectives in a company. 26:22

    • Martin emphasizes the importance of data-driven decision making in people operations, with a focus on employee happiness and retention rates.

    • Brandon and Martin discuss the importance of collaboration and continuous learning within the product development team, with a focus on embedding retros and learning outside of product.

    • Martin highlights the need for a champion within the team to drive initiatives and ensure ongoing adoption, with regular check-ins and feedback to gauge effectiveness.

  • Using "5 Whys" to identify root causes of problems in business. 30:05

    • Matt Jones shares his experience with using retrospectives to drive improvement in teams, emphasizing the importance of psychological safety and a simple five whys process.

    • He faces challenges in implementing retrospectives across different functions and cultures, citing a lack of buy-in and psychological safety.

  • Product-dev collaboration, agile methodologies, and software engineering. 32:19

    • Bethany and Martin discuss the challenge of different departments within a company not sharing knowledge and resources, despite being in the same industry.

    • Martin and Matt discuss the challenges of measuring productivity in software development, with a focus on the differences between short-term and long-term goals, and the need to prioritize creativity and outcomes over process productivity.

    • Matt argues that software engineering is a creative undertaking, and that agile methodologies can help align development with personalities and produce better outputs by focusing on outcomes rather than in-process productivity.

  • OKRs, product development metrics, and trust in the CFO-CEO relationship. 36:11

    • Brandon M suggests cross-functional OKR teams can foster cross-pollination and inspire company-wide collaboration.

    • Martin agrees on the importance of measuring developer productivity, citing deployment frequency and ticket turnaround time as key indicators.

    • Martin emphasizes the importance of security and stability in a business, while Matt Jones stresses the need for speed and delegation of authority to achieve autonomy and purpose.

    • Martin emphasizes the importance of transparency and earning trust from the CEO, citing his experience working with a founder who is hesitant to let go of their baby.

    • Matt Jones highlights the need for a mature and open relationship between the CEO and CFO, allowing for flexibility and adaptability in navigating challenges.