Viewpoint Advisory Group
I partner with tech executives to build the operating systems, strategic clarity, and AI capability that make growth sustainable — and show your teams how to build in the new AI world.
Let's Talk
About
I'm Katie Dasso — founder of Viewpoint Advisory Group and a strategic operator who has spent 15+ years helping high-growth companies build the clarity, systems, and organizational foundations they need to scale without breaking.
My career has taken me from Vistaprint and TripAdvisor to Chegg and Hummingbird Healthcare — standing up PMOs, building product organizations, driving cross-functional alignment, and partnering directly with CEOs and Presidents to turn strategy into executable reality.
I specialize in the messy, high-stakes work that falls between strategy and execution — designing operating rhythms, building accountability frameworks, aligning teams around what matters most, and creating the organizational infrastructure that lets ambitious companies grow with intention.
I also help organizations navigate the AI moment — not just by building AI-powered solutions, but by enabling teams to understand, adopt, and build with AI themselves. Sustainable efficiency comes from capability, not dependency.
I'm based in the Boston area and work with a small number of clients at a time, ensuring every engagement gets my full focus and energy.
Services
I offer fractional and project-based engagements tailored to where your company is and what it needs most.
OKR design and implementation, strategic planning, business operating rhythms, scorecards, and the accountability infrastructure that keeps leadership teams aligned and moving.
Standing up product organizations, PMOs, or portfolio management functions from scratch — with the frameworks, processes, and team systems to make them work from day one.
Embedding as a fractional strategic operator alongside a CEO or President — a trusted advisor who connects the dots across functions and moves the whole business forward.
I help organizations build for the AI era — designing AI-powered solutions and teaching teams how to build with AI themselves, driving real efficiency gains that compound over time.
How I Work
I work with a limited number of clients at a time. You get real attention, not a junior team member.
I work inside your leadership team — in your meetings, your Slack, your reality — not from the outside looking in.
I thrive in fast-moving, high-growth environments where ambiguity is the norm and the answer is usually "we need to build that."
I'm not here to produce decks. I'm here to make sure the right things get built, aligned, and executed.
The gap between a great strategy and a great outcome is almost always an execution problem. That's where I live.
— Katie DassoContact
I'm currently accepting a limited number of new clients. Let's find out if we're a good fit.
katie@viewpointadvisorygroup.com