Coaching

Coaching for every stage of your career, from your next role to your next level.

I’ve spent a decade inside the companies where careers are made. I know what gets people hired, promoted, and trusted to lead.

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Your next role

Your next level

Leadership

RecruitingCoachingBrand OfferingsThe Go-to-Market KitRecruitingCoachingBrand OfferingsThe Go-to-Market Kit

Coaching options

Four ways we coach.

Executive Coaching

For senior leaders taking on bigger scope, board and investor dynamics, or a first C-suite seat.

Leadership Coaching

For new and growing managers building teams, giving feedback, and leading through change.

Professional Development

Programs and workshops on AI fluency, communication, and career growth.

Career Coaching

Interview prep, job search strategy, offers, and negotiation.

Reviews

What Coaching Clients Say

He quickly understood my goals and helped me identify how to best leverage my strengths. A networking role-play gave me the confidence and structure I needed, which ultimately helped me land my next role.

Landed My Next Role

David is very knowledgeable about the ins and outs of the VC industry… He gave me crucial, actionable advice. I would highly recommend him to anyone looking to break into VC.

Very Thoughtful Session on Breaking into VC/PE

He helped me build a clear and effective framework for preparing and having the conversation, which really boosted my confidence. I highly recommend him if you want to feel empowered during your negotiations.

Highly Recommend David for Salary Negotiation Guidance

The Career Coaching Package: 10 sessions

Featured offerA structured program that takes you from “what’s next?” to a signed offer.What’s coveredContact us for pricing.

Hiring has changed. Your career strategy should too.

AI is reshaping how companies hire and what they expect from the people they promote. We coach professionals to prove AI fluency in the rooms that matter: interviews, performance reviews, and leadership conversations.

Show it in interviews

Talk about how you use AI with concrete examples hiring managers trust.

Get past the screen

Resumes and LinkedIn profiles that read well to both screening tools and the people behind them.

Lead teams through it

For managers and executives, guide your team through AI adoption with clarity and confidence.

Workshops for your team

Group sessions on AI fluency for your organization, delivered virtually or on-site.

FAQ

Coaching questions, answered.

What does a career coach help with?

Career coaching covers interview prep, job search strategy, resume and LinkedIn profiles, networking, and offer negotiation, so you land the right role on the right terms.

What's the difference between executive and leadership coaching?

Executive coaching is for senior leaders taking on bigger scope, board and investor dynamics, or a first C-suite seat. Leadership coaching is for new and growing managers building teams, giving feedback, and leading through change.

How many sessions do I need?

Career Coaching is a 10-session package. Executive, leadership, and professional development coaching are scoped in a free consult around your goals.

Is coaching virtual or in person?

Both. Individual sessions are available virtually or in person in Austin, Texas. In-person individual sessions elsewhere are available by request, and group sessions and workshops can be delivered on-site, with travel.

Do you coach clients outside the U.S.?

Yes. David has coached clients in 19 countries across 6 continents.

Do you run group sessions or workshops?

Yes. David has led group sessions for 800+ attendees on topics like AI fluency, communication, and career growth.

Ready for your next role or your next level?

Request a free consult and we’ll map out the right coaching for where you are.The career coaching services provided by Hollestelle Holdings are designed to offer personalized guidance and support. While every effort is made to provide accurate and effective strategies, career outcomes are dependent on individual effort and market conditions. No guarantees of job placement or specific salary increases are implied.