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EIR Spotlight: Todd Caponi

February 4, 2018


Please meet VentureSCALE Entrepreneur in Residence, Todd Caponi.  Todd is the Chief Revenue Officer at PowerReviews.


VentureSCALE: Give us a brief overview of your background working with tech companies:


Todd: I started into technology sales soon after college...starting in 1994 selling mainframe applications with Computer Associates. After floundering around the tech sales world with companies like SAP and a couple of early 2000’s startups as a pretty average sales guy, I realized my true passion was in teaching, leading, and building. I threw myself into the deep end by purchasing a sales training company. Building and running that for a few years propelled me to where I am now, having built the infrastructure as a sales leader for 3 different tech companies (2 venture backed, 1 bootstrapped). I also spent 3+ years on the sales leadership team at ExactTarget during their rise to a successful IPO and eventually a $2.7B exit to I’m currently the CRO over at PowerReviews, where we've taken the revenue team from essentially a cold start to over 60 team members in just 3 ½ years.


VentureSCALE: What's your biggest accomplishment as it pertains to scaling an organization?


Todd:  I actually won the American Business Award “Stevie” in 2009 for VP of Worldwide Sales of the Year during my tenure at a small Valley-based tech company called Right Hemisphere, beating out nominees which included the head of sales at FedEx...which was pretty cool. But I think I’m most proud of how low the voluntary turnover rate has been at every sales organization I’ve been associated with along the way. Culture wins! In the last 5 years, my average voluntary turnover rate for teams reporting through me is around 2 1/2%, where the industry average is closer to 16%. We spend too much time working not to love what you do and who you do it with...and those environments reap big rewards.


VentureSCALE: In your opinion, what is the biggest challenge today facing an early stage company in regards to growing revenue, and how would you recommend they overcome it?


Todd: I believe it’s “focus” - ensuring you’ve figured out what opportunities to spend your time on as a business. We’ve tried to establish a “no science projects” policy whenever we determined early on what types of companies, industries, geographies, sizes we knew we could (a) win, (b) drive mutual long term value, (c) won’t cause us short-term hero, long-term zero syndrome (meaning, we spend so much time winning it, we forget about everything else). There are many gravestones of companies that focused on winning a battle, but losing the war in the process.


VentureSCALE: Best sales, SaaS, Tech and/or business related books, authors, articles, podcasts or newsletters?


Todd:  I’m a total geek for the brain functions and makes decisions. Books that combine brain science with sales move the top of my list, and my long train commute into downtown Chicago just about every day often includes a podcast or two. I’m a huge fan of the concepts of “The Challenger Sale”. I’m actually writing a book (first time!) now about the next evolution in enterprise selling, the working title being “The Transparency Sale” (combining brain science and sales, of course!). I really loved the book "What Great Salespeople Do" by Michael Bozworth & Ben Zoldan and "Story Based Selling" by Jeffrey good brain science / highlighter worthy books. I also listen to Roger Dooley’s “The Brainfluence Podcast”, NPR’s “Hidden Brain” podcast and there are a couple really interesting episodes of the “Brain Matters” podcast that I can’t get enough of, too.


VentureSCALE: Do you see any interesting future trends as it pertains to growing an early stage tech company?


Todd:  There’s great news and terrible news as it relates to the midwest’s blossoming tech community. The great news is that there’s so much more amazing local talent. PowerReviews is actually the first Chicago-based tech company I’ve worked for in my 23 years in the space...because there weren’t very many just a few years ago. Now they’re everywhere. The terrible news is the war for talent is escalating. Attracting and retaining great people gets harder as the demand goes up...and finding individuals who want to take the early stage risk that aren’t demanding gigantic salaries at the beginning is a bit of a needle in a haystack.


VentureSCALE: There are big technology companies that are lower risk, pay a lot, and provide a ton of stability...all qualities human beings actively seek. Why do you and so many others overlook that choose the life of early stage tech?


Todd: For me, my passion is in the build. While a nicely full wallet & the knowledge that my job is super stable is pleasant, I get more excited about creating foundational revenue capacity where I can look back and think, “we built that!”. I always felt lost in big my contribution was so hard to see. At PowerReviews, I think back to our first few big wins, where we tackled each other in the hallways, busted out champagne and celebrated like we won the World Series. We fight battles every day that can mean the success or failure of the entire business, which bring the team together like a family. I cherish that.

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