The Winding Road to Leadership: A Case Study from ClearBank’s New CPO

Q&A: The new group chief product officer at ClearBank ascribes her remarkable career trajectory to a gritty commitment to growth, persistence in the face of obstacles, a core group of mentors and champions — and the power of being nice.

In little more than a decade since graduating Pepperdine University with a Bachelor’s in Cognitive Science, Megan (Caywood) Cooper has amassed a remarkable resume, boasting experience across startups, big tech and major banks. Her stints range from product manager at Intuit to chief platform officer at U.K.-based Starling Bank, as well as chief product officer at Barclays.

In January 2024, she was recruited as the group chief product officer at ClearBank, the London-based enabler of real-time clearing and embedded banking for financial institutions.

In conversation with Jim Marous, founder of the Digital Banking Report, Cooper traces her diverse career path and shares advice on overcoming obstacles, balancing work and motherhood, all while transforming banking as we know it.

Q: Walk us through the key milestones in your career journey so far.

Cooper: I started in fintech and Silicon Valley at Intuit, which was recommended by mentors as the ideal training ground for world-class product management. Getting that first PM role out of college was a huge milestone. Intuit was amidst a major digital transformation, so I gained great experience assisting senior leaders in that effort.

I developed niche expertise around UK regulation that enabled me to take on an expanded leadership role, building out Intuit’s UK product at Xero. After several successful product launches there, I had the credentials to move to the UK and start my own fintech.

That’s when I met Anne Boden and joined Starling to build a bank from scratch – an incredible ride. As my boss, Anne was pivotal to my growth. Having the top person as an advocate sees your achievements as reflecting well on them, so they actively mentor and promote you.

Read more on Anne Boden and Starling:

After proving digital banking at Starling, I was headhunted to Barclays to lead digital transformation. Combining my experience made me well-suited to drive change there. Now, joining ClearBank feels like the perfect next step – a scaling challenger bank focused on transforming core infrastructure.

Q: What appealed to you about banking infrastructure?

Cooper: When you and I first met years ago, many banks were innovating on front-end apps, but backend innovation lagged. Core modernization enables innovation for consumers and businesses. At ClearBank, the infrastructure itself is the focus. New technologies like cloud, APIs, and automation have huge potential to revolutionize capabilities if the foundation is transformed. I’m excited to leverage my experience to help ClearBank disrupt from the ground up.

Pivoting Between Startups and Large Firms

Q: You’ve worked at both large and small organizations. How was that experience valuable?

Cooper: At large firms like Intuit and Barclays, you build your skills and resume working with experts driving massive initiatives. You gain credibility that unlocks future opportunities.

Startups and younger firms let you take risks, like joining Starling to transform banking. Once you have experience, you can handle uncertainty better. Each environment provides complementary benefits.

I think oscillating between big and small has worked well for me. The combination of reputational clout and willingness to take chances has enabled me to have an impact across different settings.

Q: What lessons did you learn at Intuit during their digital transformation?

Cooper: Intuit’s leadership developed a brilliant digital strategy that I got to observe early on. They focused on mobile and global capabilities, areas I worked directly on for QuickBooks’ UK product.

A key takeaway was the importance of switching mindsets from maximizing transactions to truly empowering customers. Build solutions tailored to user needs, not your organizational silos.

Transformations also can’t happen overnight. Take an iterative, composable approach rather than attempting a complete rip-and-replace overhaul. Embrace pilot programs and early prototypes to test and evolve.

Why a Growth Mindset is Critical to Leadership

Q: What key mindsets fueled your rise to leadership roles?

Cooper: Growth mindset – the belief abilities can be developed through effort – was pivotal. Challenges signal the need to persist, not an innate deficiency. I want to solve problems, even if they were outside my job description, like designing prototypes to accelerate testing.

Grit and resilience were also vital. Setbacks are inevitable when pursuing ambitious goals. You must stay determined through the challenges – where there’s a will, there’s a way.

I had strong female role models, especially my grandmother, who modeled confidence and persistence. Her unwavering support gave me that voice in my head, pushing me to keep aiming high no matter what.

Q: Were there any books or concepts that strongly influenced your outlook?

Cooper: Carol Dweck’s research on growth mindset showed abilities are muscles to train, not fixed traits. This instilled confidence I could gain skills through hard work.

Similarly, Angela Duckworth’s work on grit as the key to achievement was pivotal. I constantly re-read motivational books like Seth Godin’s The Dip on persevering through exponentially growing challenges as goals get bigger.

And Randy Pausch’s thoughts on seeing obstacles as purposeful barriers to surmount, not reasons to quit, resonated deeply. I’m a firm believer that you can achieve anything with grit and a tenacious growth mindset.

Navigating Gender Bias with Supportive Mentors

Q: You mentioned strong female mentors. Can you elaborate on their impact?

Cooper: I was very fortunate to have advocates like Anne Boden, who counseled and encouraged me. Seeing other women succeed demonstrated what was possible and instilled confidence.

My grandmother set a powerful example of resilience and persistence that shaped my outlook tremendously. I draw on her strength of spirit to this day when facing difficulties.

Representation matters greatly. If you have senior leaders invested in your growth, it makes overcoming systemic obstacles much easier.

But any good mentor, male or female, who takes an interest in your development can make a big difference. Seek those willing to offer guidance to amplify your chances of success.

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Q: What obstacles did you face as a woman, and how did you overcome them?

Cooper: Early in my career, I didn’t notice gender-specific obstacles. At Barclays, there were occasional issues like older males not seeing me as an equal. Once, a man assumed I was there to take notes in a meeting when I was a peer executive.

My approach is simply to ignore skepticism, keep aiming high, and kill them with kindness. Stay focused on goals and be relentlessly pleasant with antagonists – I go out of my way to say hi or praise their work. The industry is small, so burning bridges hurts you more in the long run.

If you encounter toxicity, remember it says more about the other person than you. Seek supportive leaders invested in your growth. With grit and resilience, you can stay the course despite distractions.

Q: How did you balance rising up the ranks while starting a family?

Cooper: I was determined to fully embrace both motherhood and my career. The “motherhood penalty” of stalled advancement for women is real, but I wanted to prove it’s possible to excel at both.

I got lucky with work-from-home flexibility. Being open about wanting to start a family soon ensured I chose supportive employers.

As a mom, I lean on childcare solutions so I can maximize time with my daughter outside work hours. Most importantly, I aligned with leaders who encourage harmony between family and work. Having a high-level advocate who supported parenting made a big difference in managing both.

It’s difficult but doable. Enlist your partner, leverage caregivers appropriately, and set boundaries to protect family time. Don’t buy into the false dichotomy – with the right support, you can nurture both a fulfilling career and family life.

Q: What specific things helped you balance work and motherhood?

Cooper: My husband and I are both fully parents, so sharing duties makes juggling easier. We utilize childcare during working hours and then focus on family time nights/weekends.

I’m fortunate that my current roles allow working-from-home flexibility when needed for childcare gaps. I’m also open about responsibilities that arise so teams can plan around them.

But ultimately, I had to become comfortable setting firm boundaries and not feeling guilty about family being the priority when required. Your coworkers want you to thrive in all areas of life, not just professionally.

I remember one of my early mentors emphasized she always took her kids’ calls, even leaving big meetings if urgent. That example of boldly stating your values sticks with me. Don’t underestimate the power of parental role models.

Keys to Success for Aspiring Leaders

Q: What career advice do you have for aspiring leaders?

Cooper: First, be very clear on your goals and visualize them. Vision boards cement ambitions and identify opportunities.
Find excellent mentors. Ask leaders you admire to coffee and request their advice on achieving your aims. They’re often happy to help, even informally.

Finally, remember the industry is small. Stay kind, keep working hard, and don’t get dragged into politics. Toxicity says more about the other person. Stay focused on your own path. With grit and resilience, you can overcome setbacks on the journey to leadership.

Q: Any parting thoughts on keys to your success?

Cooper: Build diverse experience across both large and small firms to expand your skill set. Absorb everything you can from experts early on. Later, calculated risks and an entrepreneurial mindset can provide accelerated growth.

Embrace a learning mindset. Skills can be honed through diligent effort. Setbacks just mean you need more work in that area.

Never underestimate the power of strong female role models. My grandmother and managers like Anne Boden instilled confidence and persistence that I draw on to this day. We all stand on the shoulders of those who came before us.

Finally, remember that resilience is a muscle that strengthens with time. Early setbacks prepare you for greater future challenges. Stay gritty and growth-oriented for the long haul. With tenacity and a bit of luck, amazing things are possible.

For a longer version of this conversation, listen to “Profiles in Leadership: Discussion with Megan (Caywood) Cooper”, an episode of the Banking Transformed podcast with Jim Marous, available here or wherever you get your podcasts. This Q&A has been edited and condensed for clarity.

Justin Estes is an award-winning writer, strategist, and financial marketing expert with expertise in banking, investments, and fintech. His clients include the NYSE, Franklin Templeton, Credit Karma, Citi and, UBS, and his work has appeared in Forbes, Barrons and ThinkAdvisor as well as The Financial Brand.

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