Interview: Sarah McCrary, VP of Digital Strategy


The women of BPMA have been working to bring Boston Women in Product to the Metro-Boston community.  Join us at our first event where Sarah McCrary will lead a discussion on how we can assert ourselves as technical product leaders.

As we get ready for our kick-off event, we sat down with Sarah to ask some in-depth questions about her professional experiences.

First of all, thank you for taking the time to speak with us about your background!  We are very excited to have you as our inaugural speaker for the Boston Women in Product group.    Tell us, how did you get started in your career?

In my early roles working at an ISP (Internet Service Provider) during grad school and later in a telecom provider after graduation, I kept finding opportunity within the technology teams and would speak directly to senior leaders to propose projects that I thought would help us achieve more of our market objectives. I’ve written almost every one of my role descriptions.

As I established my credibility and grew my skills managing large scale, technology driven projects, I became really interested in product management; mainly because I saw the same discipline and methodology I applied to running critical technology infrastructure and application development programs were missing in my organization. Within my project plans, I began to take on more product management responsibilities.

I can see how you were able to transfer those skills managing projects into managing products. I have also found it beneficial to have strong project management skills as a foundation to planning strategy. What was the impact of this experience as you transitioned into more of a product focused role?

I influenced the organization by focusing our strategic planning around our value to our customers. This seems strange to have to point out, but the company was more focused on organizing product development and management by sales channels, not by the actual buyers. Because I was so close with our executive committee, when we acquired a high-risk start-up I was asked to help run it.

Today I’m working as the leader of a digital strategy transformation that ties together my experience in technology, product management, and building internal coalitions. Our aim is to overhaul the digital interactions we have with customers and business partners so we can deliver more value to those constituents from their relationship with us. The key to all of these roles has been directly linking real business outcomes and understanding how the customer’s experience drives those outcomes.

Unfortunately, not having the right focus on the customer or buyer tends to be more common than we would like to admit! You had the opportunity to work closely with the executive committee, but cross-functional collaboration is also important. How do you interact with the different roles across a company?

Find out what is important to the person in their role and figure out how to help them achieve their objectives, giving support will win you support for what you need to get done. Be candid and sincere about what you know and don’t know. Develop the habit of writing down the decisions you make with others and sharing it with them for clarity and commitment.

Good relationships with teams follow the Stephen Covey maxim “Seek first to understand and then to be understood.” Being clear about the team’s interests, ignoring hierarchy and focusing on how we improve the value of our offerings to our markets – personally I think about how I can get better every day.

Speaking of interacting with different roles, technology is known to have a predominantly male demographic. What advice can you give to other women looking enter or develop their career in a technology focused product field?

It is important that you can be envisioned as a leader. We face a hidden bias because women of all ethnic backgrounds are not well represented in positions of technology product leadership. Understand that, but don’t let it deter you. Only you can challenge this bias by seeking more leadership roles, taking expertise in your domain seriously, and helping to find ways to open more opportunities in your organization to women.

I see many strong women undermining their own leadership image. They pose their comments tentatively instead of with conviction; they shy away from calling out bad behaviors on their teams because they want to “get along”; and they undermine themselves by unnecessarily deferring to male colleagues for no other reason than that’s the way they’ve been socialized.

That is an unfortunate reality, but to your point we can drive change by challenging these biases. In addition, there is a lot that product professionals have to balance, from the strategic vision to the tactical execution. How can Product Managers balance competing demands while maintaining focus on the big picture?

Understand how you create value for your customers, colleagues, and the organization. What you do everyday has to be tied directly to how the company is valued by your customers and if you can’t articulate that directly, keep digging until you can. Start taking risks to make opportunity.

The PM professional has to be obsessed with the connection to the buyers and end users. By placing the emphasis on the user experience you will more clearly prioritize the research scope and technology skills required to lead and deliver.

Ultimately, the ability to maintain focus on the big picture and translate that to day to day accomplishments is really valuable. Everything else can be learned and practiced and what skills you need are highly contextual to the needs of your customers, colleagues, and organization. PM’s are coalition leaders – you have to practice influence over a tremendous breadth of strategic and tactical themes.

Driving focus on what matters within all the noise for your teams is essential so you must have a clear idea of the long-term and the immediate.

That is great advice! Before we go, what are some of your favorite resources for product management?

Pragmatic Marketing is a favorite because of the emphasis on the customer, smart use of data, and the way they matrix the many responsibilities to deliver to the market. I’ve sponsored internal training sessions with Pragmatic and also strongly encouraged team members to attend their classes.

I follow Erica Joy and Steven Sinofsky on Medium, Sue Raisty (the Cranky Product Manager) has a direct style about B2B product management and Rich Miranov has a terrific site for technology product managers at

Thank you again for your time!  We look forward to hearing more about how we can claim our value as Technical Product Leaders at our event on March 3rd.  

Sarah McCrary

Sarah arrived in Cambridge, MA to lead a small start-up through a rapid growth phase. What happened was the quick inflation and quicker deflation of a business plan, repeated pivots, and reflections on the struggle for sustainable innovation in established firms casting about to find their “Next Big Thing”.

Her product team leadership experiences includes co-inventing an encryption solution for protecting payment data (Heartland Secure e3); leading hardware and software start-up, Leaf, to build secure, cloud-based commerce solutions for small and medium sized businesses; and, currently, spearheading the digital experience transformation for a Fortune 1000 company (Heartland).

She is particularly interested in connecting businesses, consumers, and developers to make commerce easier and more secure for all.

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