I help leaders solve gooey problems.

Strategic thought partnership for founders, CEOs, and senior leaders navigating complex, high-stakes decisions.

Your hardest problems don’t have clean edges. The decisions that keep you up at night aren’t the technical ones, they’re the gooey ones. Where strategy is tangled with people, capital is tangled with timing, and the obvious move might also be the wrong move.

Flore Advisors provides sustained strategic thought partnership for founders, CEOs, and senior leaders at critical inflection points.

I don’t develop you as a leader. I work with you on the substance of what you’re actually trying to figure out. The decision, the document, the conversation, the strategy that isn’t coming together.

Coaches work on you. Consultants deliver a report and leave.

I work alongside you on the actual problem, on a sustained basis.

Let's build something meaningful together.

What I help with

Strategic Operations

Build systems that scale with your vision, not against it. At the growth stage, operational complexity compounds fast. Org design, executive hiring, leadership transitions, board and investor relations, and business development strategy all demand attention at once.

I help leaders create the infrastructure and decision-making clarity needed to run a more complex company without losing what made the company work in the first place.

Pivot Planning

The pivots that work aren’t panic moves, they’re strategic evolutions. For leaders who have already built something real, a pivot carries higher stakes: more investors to bring along, more team members affected, more to lose if the repositioning misses.

I serve as the thinking partner who helps you move on conviction rather than pressure, working through market repositioning, business model redesign, revenue strategy, and stakeholder communication with the rigor the moment demands.

Fundraising Strategy

Navigate later-stage funding with confidence and approach the right partners with clarity. At the growth stage, the fundraising conversation shifts. Expectations are higher, scrutiny is deeper, and narrative precision matters more than ever.

I help you shape how the story lands across every investor touchpoint, work through investor targeting and pitch positioning, and develop a materials strategy so you’re going into the process with a clear point of view, not just a deck.

How the work is structured

Phase One — The Landscape

SIX WEEKS · THREE SESSIONS · WRITTEN SYNTHESIS

We map the full landscape of your situation: pressures, stakeholders, history, what’s been tried, what’s been avoided. I synthesize what I hear into a written deliverable — a reframed problem, working hypotheses, and recommended focus areas — and then we decide together whether to continue.

Phase Two — Ongoing Partnership

SIX MONTHS · BIWEEKLY SESSIONS · DEFINED ACCESS

Standing 90-minute sessions, same day and time, agenda driven by whatever’s most pressing. Real work on real materials: document review, deck feedback, board prep, response shaping. Defined between-session access so the work doesn’t stop when the call ends.

For VCs and accelerators

Refer portfolio companies for advisory support. I’ll provide quarterly progress updates so you stay informed without adding to your bandwidth.
For accelerators, I can join a cohort as an embedded strategic advisor through office hours, workshops, or dedicated 1:1 sessions.
Intensive pitch refinement ahead of demo day: narrative, delivery, investor Q&A prep, and full materials review.
For portfolio companies at a specific inflection point, a targeted engagement on fundraising strategy, pivot planning, or ops build-out.

I never compete with your value-add.

I deepen it.

Origin Story

With a background spanning late-stage investing at at a large asset management firm, co-founding a global medical device marketplace, and serving on the Board of Trustees at a large research university, I bring an investor’s eye to your situation — and I know what’s on the other side of the table because I used to sit there. That perspective shapes how I help you think about strategy, operations, and capital.

Twenty years at the intersection of capital and entrepreneurship means I understand the emotional experience of building. I match honesty with warmth and the candor that moves you forward.

About Flore Advisors’ CEO

Anika Penn

Anika Penn is the founder of Flore Advisors and a strategic advisor to founders, CEOs, and senior leaders on their highest-stakes decisions. Her background spans late-stage investing at Baillie Gifford, co-founding Frontier Health (a global marketplace for medical devices), an Entrepreneur-in-Residence role supporting women-led startups, and service on the Board of Trustees at Johns Hopkins University. The child of entrepreneurs, Anika brings the investor’s eye, the founder’s instincts, and the operator’s judgment to every engagement.

Clarity

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Capital

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Operational Calm

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Clarity ✴︎ Capital ✴︎ Operational Calm ✴︎

Testimonials

“It is rare to meet people who can weave together hard truths and constructive criticism with genuine empathy and compassion. But that “tough love” doesn’t get close to capturing what it’s like to do deep-dive work with Anika. Add to the mix her keen ear for salient details, an ability to ask incisive questions that get to the heart of the matter, and a persistence that keeps a conversation on track when the tangents seem so numerous.”

— Marc S.

Let’s work together

For founders

If you’re navigating something complex and high-stakes, something gooey, and you want a thinking partner with the judgment to match the moment, I’d welcome the conversation.

For VCs and accelerators

If you’re a fund or accelerator looking for a trusted resource for your portfolio, let’s talk about how Flore can support your founders.