Ink & Sky was founded by strategist and connector Karen Toste after more than two decades working at the intersection of strategy, relationships, communications, and growth.
Across technology, financial services, philanthropy, and social impact, Karen has built partnerships, launched programs, mobilized resources, created high-impact experiences, and helped ambitious ideas move from possibility to reality.
PAST EXPERIENCE
Deep experience across innovation, capital, and community.
The throughline is relationships.
Different sectors. Different organizations. Different challenges. But the work has always come back to the same thing: bringing the right people, ideas, and opportunities together to move something forward.
Karen has seen how a single introduction can open a door, how the right partnership can accelerate growth, and how a thoughtfully designed experience can create opportunities that wouldn't otherwise exist.
That perspective shapes how Ink & Sky works today.
20+
Years of experience
$60M
Funding influenced
150+
Events + convenings
75+
Strategic partnerships
Experience spans organizations including Silicon Valley Bank, The Tech Interactive, American Red Cross, and The Leukemia & Lymphoma Society, with work across innovation, venture, philanthropy, technology, and social impact.
Experience & Impact
How we work.
Ink & Sky brings an outside perspective without staying on the outside.
We sit alongside leadership to untangle complicated challenges, see connections across seemingly separate opportunities, and identify what matters most. Then we roll up our sleeves and help make it happen.
No layers. No one-size-fits-all playbook. Just senior-level thinking, hands-on support, and a focus on moving the work forward.
About Karen
Karen is a strategist, connector, and builder with more than 20 years of experience spanning innovation, financial services, philanthropy, and social impact.
Before founding Ink & Sky, she led Catalyst 2045 at Silicon Valley Bank, building partnerships and programs that connected founders, investors, corporate leaders, and other partners across the innovation economy.
Earlier chapters of her career included The Tech Interactive, American Red Cross, and The Leukemia & Lymphoma Society.
Based in Portland, Oregon, Karen works with organizations across the country.