Available for new clients

Executive Coaching
for leaders playing
at the highest level.

I help executives, founders, and leaders unblock what is stopping them from achieving their most ambitious goals.

Background includesCMOFounderExecutiveFortune 100 (x2)Pre-Seed to Series C

My Stats

Real experience.
Not just concepts and questions.

CMO
Lived experience leading my function
Pre-Seed → Series C
Founder, executive, and advisor experience
Fortune 100 (x2)
Led teams at Salesforce & Chevron
18 Years+
GTM experience

About

A coach who's been in your seat.

Taylor Hollenbeck

Executive, then Coach.

Before transitioning full time into coaching, I built a 17+ year career as a marketing executive — leading teams, building functions from scratch, and navigating the pressure of high-stakes growth.

“I understand the terrain because I've walked it.”

Most recently, I was the Chief Marketing Officer at SecurityHQ, a cybersecurity company with 600+ employees across six global locations. Prior to that, I served as Head of Marketing at Lilt, a Sequoia-backed AI localization company, from Series A through Series C.

My career has taken me across the full product and go-to-market lifecycle — in marketing, sales, and product roles — and across companies of all sizes, from Fortune 100 companies like Salesforce and Chevron to founding a company and being employee #5 at a YC-backed startup.

I've also founded my own company, giving me hard-won perspective on what it actually takes to build something from nothing. That breadth — across functions, company stages, and contexts — is what I bring into every coaching engagement.

Who I Work With

Built for leaders
playing for real.

Two primary client profiles — both at inflection points where the right coaching meaningfully changes trajectory.

01 · Startup Leaders

Founders & Executives at High-Growth Companies

Leaders navigating the demands of building at speed — where the org is changing, the stakes are high, and every decision carries weight.

  • First-time executives stepping into C-suite roles
  • Founders scaling beyond the early team
  • GTM leaders building a repeatable motion
  • Leaders managing boards and investors

02 · Corporate Leaders

Directors through SVPs at Fortune 1000 Companies

Mid-to-senior leaders ready to move from high performer to recognized executive — navigating complexity, driving influence, expanding impact.

  • Leaders stepping into new or changing roles
  • Leaders managing large, complex organizations
  • Executives in periods of transformation
  • High-potentials being developed for senior leadership

Approach

Direct. Structured.
Results-oriented.

Whole-Person Clarity

We start with the full picture. Real change happens when you understand the patterns, not just the presenting problem.

High-Stakes Focus

We work on what actually matters — the goals, decisions, and relationships with the most leverage on your trajectory.

Honest Partnership

I'll tell you what I see, even when it's uncomfortable. The most useful coaching conversations aren't always the easiest ones.


My Why

Paying It Forward

I know it, because I lived it.

I have felt the pressure of putting on a brave face for my team while my world was otherwise crumbling around me.

“I know what it is like to carry the weight of personal and company pressure, self-doubt, imposter syndrome, and fear.”

I have had the hard conversations with CEOs, board members, peers on the executive team, and members of my team. I have hired, fired, coached up, and coached out team members. I have been part of teams that have excelled beyond anything I thought possible.

I have been through reorgs, pivots, and fundraises. I have stripped down and rebuilt teams. I have gone through company shutdowns and acquisitions. I have experienced burnout and failure.

I know what it is like to go through these problems alone.

And I know what it is like to go through them with support.

I want to be part of that support system for you.

Get Started

Start with a conversation.

A 30-minute discovery call. We'll talk about where you are, where you want to go, and whether working together makes sense. No obligation.