DWDana Whitfield (325) 555-0125
Two companies built and sold

I have made the mistakes you are about to make

I built and sold two B2B software companies and now spend my time helping early stage founders get pricing, positioning and the first ten hires right.

2companies founded and sold
31angel investments
14 yrsoperating experience
6advisory seats at a time
How I help

Three ways I work with founders

I keep a maximum of six advisory relationships so the ones I take get real attention.

$750

Single strategy session

Ninety minutes on one specific problem, with written notes and next steps sent within a day.

$3,000 per month

Monthly advisory

Two calls a month plus async access, focused on pricing, go to market and hiring decisions.

$2,400

Pricing teardown

A two week engagement reviewing your pricing, packaging and win loss data, ending in a recommendation.

$25k to $100k

Angel investment

Pre seed and seed checks in B2B software, usually alongside a small advisory commitment.

Free

Founder office hours

Two Friday slots a week, thirty minutes each, first come first served for any founder.

Equity only

Board or advisor seat

Standard advisor equity over two years, for companies where I am already deeply involved.

Background

Fourteen years building, two exits, a lot of scar tissue

I started my first company, a scheduling tool for clinics, out of a Capitol Hill apartment in 2011 and sold it in 2016. The second, a compliance platform, I ran to 60 people before an acquisition in 2022. Since then I have angel invested in 31 companies and advise a small number of teams closely.

•Both companies were bootstrapped past $1M before raising anything
•I do not take advisory work in a category where I have an investment conflict
•Every engagement starts with a paid session, so we both know it is useful
A young entrepreneur gives a presentation on startup strategies indoors with a flip chart.
Reviews

What founders say

“Dana rewrote our pricing page in two hours on a call. Our average contract value went up 40 percent in the next quarter and we did not lose a single deal over it.”

Omar H., Founder, B2B analytics

“She told me not to make a VP hire I was sure about. Eight months later I understood why she was right.”

Kate L., Founder, healthtech

“The office hours slot is free and she gave me a full ninety minutes when it ran long. That is why I sent her four other founders.”

Diego M., Founder, logistics software
FAQ

Working together

What stage of company do you work with?

Pre seed through Series A B2B software, generally between $0 and $5M in revenue. Below that the free office hours slot is usually the right fit. Above that my operating experience gets less directly relevant.

Do you invest in every company you advise?

No, and I keep them separate on purpose. Advisory is paid in cash or advisor equity, and investment decisions are made independently. If I am considering both I tell you up front which conversation we are having.

What happens on the first call?

You send me context ahead of time, we spend ninety minutes on the single hardest thing you are facing, and I send written notes within a day. Most founders come for one session and about half turn into ongoing work.

How do I get an office hours slot?

Two thirty minute slots open every Friday and I post them on the essays page each Monday. They are free, first come first served, and I do not screen by traction or who introduced you.

Contact

Start with one conversation

Send me what you are stuck on in a paragraph. If I am the wrong person I will say so and try to point you at the right one.

Phone(325) 555-0125
Address1201 Second Avenue, Suite 900, Seattle, WA 98101, Seattle, Washington
HoursAdvisory calls Tue to Thu, 9am to 4pm PT
AreaSeattle based, works with teams remotely