Dana Louie is a thinker, builder, strategist, advocate, and most importantly operator. She previously sat in between HubSpot’s multivariate growth ambitions and its sprawling SMB ecosystem and is now serving as the Director of Strategic Programs at InvoiceCloud.
Dana hails from Colorado Springs and moved to the East Coast to attend Wesleyan, where she was a distance runner. She credits her success at rapidly growing companies to the high energy, commitment, and grit she learned as an athlete.
Her parents – an engineer dad and artist and teacher mom – helped her develop a strong foundational work ethic, dose of creativity, and analytical approach to problem solving.
She studied Math and Economics at Wesleyan, and through the school’s Quantitative Analysis Center, she was introduced to the economic consulting firm Analysis Group. She joined them upon graduation where she focused on large scale finance and antitrust litigations. Intellectually demanding and analytically rigorous, Analysis Group taught her a lot and provided her the opportunity to work with some awesome female mentors who helped her build and grow her career.
But Dana wanted to break into tech. She applied to business school and attended Harvard Business School in order to parlay her existing analytical skills with general management for a career in Product Management. She interned at Boston-based Indigo in a PM role but found she was more drawn to general management and operations.
Dana joined HubSpot first as part of a rotational program for MBA graduates, acquiring wide exposure to a variety of cross functional experiences within FP&A, Product Management, and Product Operations. She helped on projects like pricing and packaging for a freemium product launch. Unsure what she wanted to do next, she sought a rotation on the Ventures team, HubSpot’s Corporate Venture Capital arm to try something new.
Enjoying the work, Dana joined the team after the rotation and worked broadly across the Corporate Development team in both M&A and Ventures. Dana raced to come up to speed and threw herself headfirst into diligence work and writing investment memos (shout out to Hightouch the first investment she led). Through her time on the team, she learned to think creatively about the intersection of HubSpot’s existing product roadmap and future needs. Both an investor and a strategist, much of Dana’s time focused on planning and executing a corporate development strategy, including understanding the key areas for investment at HubSpot.
Seeking to move toward a high-impact operator role, Dana joined InvoiceCloud as their Director of Strategic Programs soon after the company had been taken private in a private equity buyout in January of 2024. InvoiceCloud is a leading provider of digital payment, customer engagement, and outbound disbursement solutions. At InvoiceCloud Dana is reporting to their CEO and focused on executing strategic initiatives to enable growth and efficiency.
Dana helps lead a variety of initiatives to make the company more valuable, leveraging playbooks from the company’s investors, her own experience, and the support network around the company. She helps oversee the planning around cross functional strategic projects plus the tracking of progress against their goals. This can be anything from Go-to-Market initiatives to improve sales productivity, to People and Talent Development initiatives to build on the company culture. It’s a balancing act of holding in mind the high-level strategic objectives and the nuts-and-bolts tactical plans to get there. In her own words, Dana derives energy and enjoyment from taking a company goal, breaking it down into a plan, and working with teams to accomplish the milestones to get there. At InvoiceCloud she gets to do that at a fast clip given the pace of growth.
In addition, Dana has Chief of Staff-like duties, including running weekly executive team meetings, monthly All Hands company meetings, board meeting prep and even offsite planning to help support the executive team.
She loves anchoring her career and life here in Boston. Dana has optimized for The Hub coming out of graduate school to be close to family, friends, and its talented ecosystem of builders. We’re lucky to have you!
Executing a Strategy – Negotiation, Getting Buy-In, and Driving Alignment
The scrappy distance runner who ran a few extra miles to pivot from corporate development to InvoiceCloud has learned that “everything in life is a negotiation.” She’s not just talking about deal terms. Everything she’s done – from consulting to venture investing and even now in her work at InvoiceCloud – has been tied to creating value and seeing how much of it makes sense to capture and share. Framing goals and obtaining buy-in is a critical part of that process.
To Dana, success comes from having a plan and doing what you say you are going to do. Having a clear analytical approach helps drive alignment for Dana and her teams as they make strategic decisions.
Career Insights / Learnings
Advocating for Yourself – “I’ve found that working hard only gets you so far. Knowing what you want and using your voice to get there is critical to successful career growth.”
Aligning Your Values – “What do you want from your career experiences and how do you plan on living your life? If you want to build a life that balances ambition, health, family, and friends, aligning your career to match those personal goals and career ambitions is a must.”
Finding Your Fit – “I’ve been in positions where I felt I had to change who I was to succeed. For example, I’m a naturally extroverted person who likes to make friends with my counterparts, but I’ve been in high-stakes negotiation roles where ‘being kind and relatable’ was seen as a downside. Big surprise, that wasn’t the right role for me! Figuring out your true strengths and finding a team that will appreciate you for them will allow you to thrive.”
Dana loves the interplay of strategy and operational execution in her role and career. Whether it’s at InvoiceCloud or elsewhere she aspires to a “Head of Strategy” type role in tech. She’d also love to one day teach others, perhaps as a business school professor, leading a fulfilling life inside and outside the workplace.
If you want to learn more about Dana, you can find her getting buy-in for strategic initiatives at InvoiceCloud, running the Boston Marathon next spring, and above all supporting her business partners, family, and friends. Thanks for sharing. Excited to see the trails you blaze across the Boston tech ecosystem in the years ahead!