was a very key time in my early career, being the first software startup I’d ever worked at. PayScale is the leader of cloud compensation data and software based out of Seattle, WA and boasts more than 5,000 customers. I joined the team in August of 2011 as an Account Executive on a new team focused on small accounts. The five-and-a-half year ride was one to remember. I saw the company grow from 65 to 400+ employees, including growing from 15 to about 120 sales reps. I recount what it was like selling on each team and seeing the company grow throughout various stages.

Selling to Small Accounts

The small business team was born just weeks before I was hired onto it. Our industry was very new to smaller companies who guessed, Googled or talked with candidates about their pay. It was quite the art to sell a complex solution through a mere Office Manager to their boss – the CEO. Nevertheless, as our team grew rapidly, we continued to crush our goals and build out a whole new segment of the revenue channel.

Value-selling & white-glove services

At the time, we only had “core” teams (east and west) and small biz teams. I was promoted to join the west coast team as it soon expanded to a round-robin system as opposed to territory based. Time and time again we would come up against inexpensive competitors whose data couldn’t hold a candle to ours. We had to really help our customers see the value of getting compensation right. Part of this challenge was met with some professional services. These compensation consultants gave us one of the most robust packages on of data, software and services on the market. We learned to sell at premium prices for these services and I began gravitating toward larger and larger whales.

Forging into new territory – Large Accounts

As the sales team had grown to close to 90 reps, I was offered a spot on the new team called, “Large Accounts”, where we sold to the upper-mid and enterprise customers. Because our industry was relatively new, each year we systematically raised prices to test the limits of the market and continue to drive the business towards healthy growth. We marched out against tall quotas and a few more competitors who were “rolling back prices” to take market share. Simultaneously, our customer had changed, making it harder to sell a product that partially replaced some of their job. It was exciting to be fighting for something you believed in – yet knew customers had to make a stretch pitch to sell it internally.

Moving from Venture to Private Equity backers

I still remember the day we celebrated when Warburg Pincus invested $100 million into the business to grow us for the long haul. I could definitely sense the frugality and restraint we operated under (while still having a bunch of fun) when we were venture-backed, but things had now changed. With Warburg behind us, we took some major strides and continued to grow all our teams, even acquiring another player in our place to achieve market dominance. I remembered how much our CEO reminded us that Warburg is all about investing in people and seeing the teams succeed, not burnout. This is a value I will take with me into my next venture.

I know there have been many terrible stories that have emerged from startup life and I’m sure mine was tainted because I was a top performer and made it to President’s Club (the annual celebration for top sales reps) 4 out of 5 years I sold for them.

Yes, we experienced some bumps along the way, like setting prices too high, trying out new products that didn’t catch and routinely changing processes, tools and procedures. Through it all, the leadership was committed to our success. There were many meetings where they re-set our expectations, re-focused our efforts, and empowered us with promotions, tools and flexibility. There were times people gave up and had to leave for different reasons, but through and through many of us knew that we were well supported.

That’s why for so many years, I ignored all the LinkedIn messages from recruiters – because I knew PayScale was such a great product, great team, great compensation and great company.
If everything continued well for me, the only way I could leave was if I started my own company. And that’s precisely what I did. I’ll dive into that a little during the next post.

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