How Women in SF Tech Are Building Stronger Pathways to Leadership

Leaders from Finch, Coupa Software, PagerDuty and Collectly reflect on the skills, mentors and opportunities that shaped their success and how they’re paying it forward to others.

Written by Taylor Rose
Published on Oct. 27, 2025
A collage of two women by a laptop in front of a green background to show the idea of women in tech.
Image: Shutterstock
Brand Studio Logo
REVIEWED BY
Justine Sullivan | Oct 27, 2025
Summary: Women in the San Francisco tech ecosystem are creating clearer, more accessible pathways into leadership by harnessing mentorship, building strategic networks, and stepping into opportunities as they arise. Their journeys highlight the importance of visibility, self-advocacy, and structural support in advancing into senior roles.

Women face a lot of battles for equality in the workplace, but in the field of tech it’s even more arduous. 

Compared to other industries, tech has the lowest representation of women — just 32 percent of hardware jobs and 43 percent of software jobs are held by women at the entry level. The number drops the further up the career ladder you go. 

That’s why seeing women in tech leadership positions is so important. Girls Who Code is all about providing role models.

“You can't be what you can't see,” Reshma Saujani, the founder of Girls Who Code, is quoted as saying.

Built In spoke with four women tech leaders about how representation and mentorship were critical footholds in their career climb. 


 

Alaina Jones
Sales Manager • Finch

Finch provides a unified API for employment systems. 

 

Describe your career journey so far. What skills and experiences have you acquired along the way that have helped you get to where you are now?

I’ve always been drawn to building — teams, GTM motions and companies. My career began in sales and customer success at early-stage startups, where I learned how to grow enterprise accounts, sell consultatively, leverage data, stay scrappy and adapt quickly to change.

That foundation prepared me to launch my own early-talent marketplace and later join two founders as the first business hire to lead the full customer cycle in the middle of COVID — an experience that tested every skill I had and taught me new ones fast.

I’ve seen nearly every stage of building a business from the ground up. Along the way, I’ve learned how to turn complex problems into repeatable systems, build and coach high-performing teams, translate messy customer feedback into product strategy and align fast-moving, cross-functional teams around shared goals.

I’ve also learned that a career path is rarely linear — sometimes a step back or sideways is exactly what propels you toward the next big opportunity.

 

What support did you receive from individuals or resources that helped you step into a leadership role?

I was fortunate to have an incredible string of first bosses — both women and men — who balanced high expectations with trust and autonomy. They gave me room to be creative, embraced my wacky ideas and took ownership when things didn’t go perfectly. Those early experiences built my confidence and taught me what strong, empathetic leadership looks like — lessons I carry with me to this day.

As my career progressed, I made a point to build a network of trusted people I could turn to for advice. I’ve stayed connected with former managers, sought out women one level ahead of me for tactical guidance and worked with a leadership coach to strengthen my management and communication style.

At Finch, I’m continually inspired by the women on our leadership team who model what it means to combine execution, authenticity and clarity. Having that mix of sponsors, peers and role models has made all the difference — it reminds me that leadership growth is never something you do alone.

 

How do you encourage other women on your team to become leaders themselves? Are there any stories you can share that showcase how you’ve done this?

I encourage every woman who wants to lead to focus on three things: Be visible, advocate for yourself and build scope. 

Visibility means creating moments to showcase your work and connect with leaders across the organization. Advocacy means being clear about your goals — don’t wait until review season to talk about what you want next. And building scope means taking initiative. If you see a gap or opportunity, raise your hand (or don’t) and run with it. Even if it doesn’t go perfectly, it shows ownership and ambition — qualities every great leader has.

To create more space for this kind of growth, I started the Finch Women’s Group — a community built around monthly socials and quarterly professional development sessions. Two and a half years later, it’s become a space where women at every level showcase their work, overcome imposter syndrome and celebrate each other’s wins.

To me, leadership is about spotting potential early, creating room for others to grow and helping them see what they’re capable of long before they see it themselves.


 

Mel DeWald
Enterprise Program Manager (ePMO) • Coupa

Coupa Software is an AI company that created a total spend management platform for businesses large and small. 

 

Describe your career journey so far. What skills and experiences have you acquired along the way that have helped you get to where you are now?

The economic downturn in 2008 forced my career to take an unexpected turn. I had to quickly pivot from my profession, earning new certifications and acquiring a wide range of skills to qualify for a different field. While this change was frustrating and intimidating, I was fortunate to have a strong foundation of underlying skills that made the transition possible.

With the support of mentors and friends, I learned to be more adaptable and flexible. This experience taught me the importance of enhancing my soft skills and focusing on building relationships, which are now key assets in my career.

 

What support did you receive from individuals or resources that helped you step into a leadership role?

I’ve had the privilege of working with and for some incredible leaders, both women and men, throughout my career. They taught me the importance of building strong relationships and focusing on my soft skills, which have been invaluable throughout my professional journey.

These leaders also equipped me with the tools and knowledge to become a great people manager and mentor. By partnering with my teams and creating a safe space for them to learn and grow, I’ve empowered them to manage up and provide valuable input that contributes to our collective success.

 

How do you encourage other women on your team to become leaders themselves? Are there any stories you can share that showcase how you’ve done this?

Encouraging other women to become leaders is a crucial part of building a strong, inclusive and thriving workplace.

I’ve found that one of the most effective ways to do this is by acting as both a mentor and a sponsor. As a mentor, I provide advice, guidance and support while actively advocating for other women on my team.

A key part of this is helping them build a professional network. Networking is vital for career advancement, but building meaningful connections can be challenging. As a leader, I try to help by making introductions and creating opportunities for them to connect with senior leaders and peers they otherwise might not meet.


 

Amy Aycock
AVP, Sales • PagerDuty

PagerDuty is a global leader in digital operations management, enabling customers to achieve operational efficiency at scale with the PagerDuty Operations Cloud. 

 

Describe your career journey so far. What skills and experiences have you acquired along the way that have helped you get to where you are now?

When I started in tech, I didn’t even understand what software was. Fortunately, my employer invested in comprehensive training that built upon the foundation my father — a sales professional and author — had given me. He taught me that success stems from building trust by answering three unasked customer questions: Can I trust you? Are you committed? Do you care about me?

Unlike many salespeople who rely on “the gift of gab” and generic pitches, I learned that listening matters more than talking. Years of customer meetings, negotiations and implementations helped me develop my skills, complemented by training programs and books. There’s no replacement for practice — you improve through repetition.

I approach every interaction guided by three principles: Do what’s right, do your best and treat others as they want to be treated. This customer-focused approach has been the cornerstone of my success in building lasting relationships and driving results throughout my career in technology sales.

 

What support did you receive from individuals or resources that helped you step into a leadership role?

I never aspired to leadership until my manager — a talented leader who built a top-performing team — approached me about a first-line role and offered his sponsorship. With his coaching, I received the Leadership MVP award that year and my team won top enterprise team the following year.

Great mentors have been essential to my growth. My network includes diverse leaders with different experiences whom I can ask questions and soundboard ideas. Some have become friends, others business acquaintances, but all model expertise I value, including balancing demanding careers with fulfilling personal lives. Approaching these conversations with curiosity, vulnerability and self-awareness has been game-changing.

PagerDuty invested in me with a career coach, continuous training and stretch opportunities. When our CRO called asking me to lead EMEA sales temporarily, I felt excitement mixed with uncertainty and fear. I was transparent and he explained why he believed in me and promised support. I’ve learned that admired leaders didn’t get there alone — they’re products of countless people who believed in them and invested their time, wisdom and energy.

 

How do you encourage other women on your team to become leaders themselves? Are there any stories you can share that showcase how you’ve done this?

A vice president once shared wisdom that shaped my leadership philosophy: “Leadership should be a pull, not a push.” Rather than forcing your way into leadership roles, be pulled through sponsorship and recognition from leaders who see your impact.

This drives how I develop women on my team. You don’t need a title to lead — opportunities present themselves daily and I encourage seizing ownership of projects requiring commitment and the ability to inspire others.

One sales rep excels at orchestrating cross-functional teams and building pipeline, so I asked her to lead training for our entire North American field team. Another rep deeply understands customers’ businesses, so I invited her to join a company-wide project defining our customer journey to accelerate value realization. By creating platforms for sharing expertise, I provide broad exposure that showcases their natural leadership abilities.

When asked about getting promoted, I share what I’ve learned: when you’re doing your job well, you don’t need to self-promote. Say yes to opportunities that let you share your story, actively help others succeed and recognition follows naturally when you focus on creating value for others.


 

Jessie Koester
VP of Customer Success and Operations • Collectly

Collectly is a fast-growing healthcare tech startup that built an AI-driven RCM software platform that increases revenue, cuts support calls and keeps patients happy.

 

Describe your career journey so far. What skills and experiences have you acquired along the way that have helped you get to where you are now?

My career has been a mix of customer success, operations and strategy roles that gave me a holistic view of how businesses grow and scale. I started in customer-facing roles, which taught me the importance of empathy, active listening and building relationships rooted in trust. From there, I moved into operations and leadership positions where I learned how to balance customer advocacy with business needs. Along the way, I honed skills in process design, data-driven decision-making and cross-functional collaboration. These experiences taught me that sustainable growth comes from building scalable systems while empowering people. The ability to navigate both the “human” and “operational” sides of business is what has propelled me into my current role as vice president of customer success and operations at Collectly.

 

What support did you receive from individuals or resources that helped you step into a leadership role?

Early on in my career, I expressed interest in leadership and got put into a leadership program by my company which propelled my learnings on what it truly means to be a leader. That program opened my eyes to the fact that leadership isn’t just about driving results — it’s about inspiring and developing others. It gave me practical tools for coaching, communicating and managing through change, which I still use today. Beyond formal programs, I had managers who were generous with feedback and pushed me to step into stretch roles even when I didn’t feel 100 percent ready. They helped me see potential in myself that I might have overlooked. Those experiences, paired with seeking out mentors and peers I could learn from, built my confidence and gave me a strong foundation to grow into bigger leadership roles.

 

How do you encourage other women on your team to become leaders themselves? Are there any stories you can share that showcase how you’ve done this?

One of the most valuable lessons I’ve learned in my own career is how to advocate for myself and ask for what I want — whether that’s a new project, a promotion or more support. I try to pass that on by encouraging women on my team to get clear about their goals and voice them openly. When someone tells me they want to grow, I work with them to map out the skills and experiences they’ll need, then create opportunities for them to get there. 

For example, someone on our recruiting team mentioned she was interested in HR. I encouraged her to start SHRM training now so she’d be prepared for when we decide to open a formal HR role. Not only did this give her a clear action plan, but it also showed her that advocating for what she wanted could create future opportunities. Empowering others to take ownership of their development — and reminding them they’re allowed to ask for what they want — is one of the most rewarding parts of leadership for me.


 

Responses have been edited for length and clarity. Images provided by Shutterstock or listed companies.