Ryan Hollander


Clipboard Health is pretty picky about hiring, so I’m guessing there were plenty of other places you could have worked. What made Clipboard stand out?

I learned about Clipboard Health when George Markoulakis, our Head of Product, reached out.  Instantly I was attracted to the rigor of the work.  During the interview process, I saw work documents from Clipboard team members.  The authors envisioned detailed customer experiences, stated metrics to track progress, anticipated reasons for failure, and planned how to coordinate with internal teams.  I knew that I would learn a great deal from the team at Clipboard Health.

I also was attracted to Clipboard’s fast pace.  When I met Natalia Perellón, who was then a senior product manager, she described her work.  I assumed that she was describing her past year, but in fact it was just her past month.  Once I realized that, I knew that joining Clipboard Health would be a way to pack decades-worth of experience into each year.

How did that bear out in practice in your product work?

My first project at Clipboard Health was to launch InstantPay.  The feature enables nurses to get paid immediately after completing a shift rather than waiting days, weeks, or longer.

I worked with a team to release the first version within a few weeks.  Improvements were made over the subsequent months.

On that project I learned Clipboard Health’s process for product management, which George developed.  The process includes dashboards to monitor for irregularities, checklists to make sure that the roll-out goes smoothly, and frequent conversations with customers.

Tell me about your transition from the product team to Head of Sales.

One of my favorite parts of Clipboard Health is that the company encourages “tours of duty.”  Team members can try a different role for two weeks to three months or or even longer.

I asked to spend two weeks making sales calls in order to understand the needs of healthcare facilities.  Shortly thereafter, I was asked to manage three sales managers, and eventually, to become the head of sales.


For someone who might want to join the sales team, what would they experience when working with you?

When people join the sales team, they complete a week-long training program.  They listen to examples of model sales calls and engage in role plays.

When managers join, they’re given a preemptive 90-day review.  This is a document that’s written from the perspective of 90 days in the future and describes what the manager will have accomplished.

One of Clipboard’s norms is to “touch reality”, which means to experience what customers and prospects experience.  Team members frequently listen to calls and read emails sent to our customers and prospects

We try to be scientific about optimizing sales.  For example, a typical project begins with a two-page document explaining what number in the sales funnel we want to move, and how we’re going to move it.  We constantly run A/B tests to find which controllable inputs have the greatest impact on sales.  Then we train to execute consistently.  We rely heavily on role plays and feedback on calls.

What kind of opportunities do you see for team members in the near future?

Because of the company’s growth, there are frequent opportunities to work on new projects.  For example, during the past six months, we created teams to work on multiple new healthcare verticals as well as new functions, such as sales recruiting.


Is there anything else you would like to share?

I was drawn to Clipboard Health in part because the company is helping nurses.  Nurses have been heroes during the pandemic for helping patients, and by extension their families, in their times of need.  Clipboard Health allows nurses to earn substantially more income.  By matching nurses with facilities, it also enables patients to receive much needed care.

We have a special opportunity to make a positive impact.  If you’re looking to do that while also growing rapidly and building a dynamic business, I hope you’ll apply to join our team.

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