Hard Earned Lessons Learned From a Former Founder

A few months ago I officially moved out of the CEO role at Appirio, a services firm I co-founded more than 12 years ago to take on the role of Global Culture Officer at Wipro. Wipro acquired Appirio in 2016 so I still get to stay in the family but I’m more of an in-law now. It’s been a big transition, and while I’m enjoying my new team and the focus and freedom that comes with this new role, the separation has made me a bit nostalgic and reflective of my 4,300(ish) days at the helm of Appirio.

Before I get too far into this next phase of my career, I thought it’d be useful to capture some of my biggest lessons learned as a founder and CEO of a start-up. A start-up that grew into one of those mid-size companies that experienced the inevitable ups and downs of those “awkward adolescent years” and that was eventually acquired by a global behemoth that had bigger but different goals than our not so small start-up.

I’m writing this not only for other founders who may be somewhere along this journey but also for my future self... so I don’t forget what I loved about the ride and what I royally screwed up.

1. Stay relevant, but stay focused.

I will never forget the words of one of Appirio’s earliest employees when he told me, “Chris, you have one job and that is to keep us relevant.” I’d say we did a decent job of this over 12 years, expanding into different regions, different markets, taking on new partnerships, and exploring new ways of working. But certain choices we made also distracted us and, to be honest, probably cost us market share and degraded aspects of our company culture.

I’ll give you an example. When we started Appirio we were very clear about wanting to be a products AND services company. The early VCs we pitched were rightfully skeptical about our ability to do this well, as so many others had tried and failed. “Pick one and optimize for that,” they said. We didn’t and we persevered with our vision because we thought times were different and we were different. It turns out we were pretty good at developing technology but even better at delivering services. It also turns out there was truth those VC warnings.

As a first time CEO, you’re also getting wined and dined like never before, rubbing elbows with people you only read about before.

It’s hard to be truly GREAT at multiple business models in a company’s formative years. We eventually divested our primary product to FinancialForce, which became the foundational for what is now their very successful PSA product. We did create a pioneering crowdsourcing platform (first with CloudSpokes, then with TopCoder) but we had services in our DNA. I wonder if we had stayed 100% focused on cloud-based professional services -- without splitting our team and our focus -- if we would have grown faster, been more market dominant longer and provided better outcomes for our customers.

Acquisitions were another miss in my book. They say M&A is hard, but we batted .285 in that department. That isn’t actually all that bad based on industry statistics, but the calories, friction, ROI, ability to deliver against expectations, and most importantly, the distractions from running the core business weren’t worth it in the long run. If I were to do it all over again, I would do fewer deals closer to our core business where we could better control the culture.

2. Don’t let swagger switch to cockiness.

There is something exhilarating about a startup and those first years of being CEO. You’re building a team that is almost a family. A team that is as passionate and driven as you yourself are about making something big happen - in Appirio’s case it was accelerating adoption of cloud computing in large companies. My co-founder Narinder Singh has a great blog series that captures this era and how we flaunted our differences and poked fun at the bigger companies that had long dominated our space. As a first time CEO, you’re also getting wined and dined like never before, rubbing elbows with people you only read about before.

I will never forget the day in 2012 when I found out Appirio was selected as a Tech Pioneer by the World Economic Forum and that I’d be able to attend the WEF events in Davos and Dalian. Or hanging out and trading stories with Frank Quattrone at some investor event (his stories beat mine hands down). When you’re riding the wave it’s easy to get caught up in the success and forget to stay humble. It’s hard to remember you’re not a special snowflake and to stay grounded alongside the team and the people who got you there. Make sure to surround yourself with people who will snap you back to reality if you start floating toward that ivory tower (and be open to the criticism when they do).

3. Build (and use) your Board wisely.

I was fortunate to have a boardroom lineup that many founders and first time CEOs dream about: Jim Goetz (who topped the Forbes Midas list for many years); Jeff Richards (former founder and one of the best marketers, speakers and advocates for a portfolio company I’ve seen); Gary Reiner (former CIO of GE and director at CitiGroup with an unbelievable), Brett Rochkind (former investment banker who is great at both numbers and business); Matt Thompson (current EVP of Worldwide Field Operations at Adobe who successfully shifted their business into the subscription era); Jeff Epstein (former CFO of Oracle who can dive into the details but still stay high level when needed), and my fellow co-founder and visionary Narinder Singh. From day one it was a heavy hitting and “full contact” (a Goetz-ism) experience and I could not be more grateful for the chemistry and eventual friendships that developed across this team, and the counsel they provided me over the years.

But while a CEO ultimately works for the board, they should also work for you. After all, they’re invested in the company as well. One of the things I’m most proud of is how we gamified our board’s revenue contributions by tracking and being very vocal about the deals they helped influence, source and close alongside our sales team. Over the years, we’d trend between 15-30% of all pipeline and deals being Board Influenced Revenue or BIR. Reach out to me directly if you want the template or want to know which board member was lifetime BIR champion. =)

Approximately every other year, for 10 years, I made at least one bad executive hire which set us back in some way - some further back than others.

4. Team first. There’s an overused saying that your people are your greatest asset. It’s overused because it’s true. Some of my greatest achievements and biggest misses relate to team. Let’s start with the achievements before I move on to where I missed.

The best thing my founders and I ever did was to be very explicit about our mission as a company (why we excited besides to make money) and the the values we wanted in our people. We hired against those values and managed against them.

When it came to hiring, we had a rule early on that co-founders had to interview (and had veto rights) on our first 100 hires. We knew they would set the bar for the next group of people we hired and we needed to keep that bar high. We invested in their experience at the company because we knew high performers had high expectations. We had a technology policy that ensured every employee was armed powerful laptops, flat panel monitors, high-end headsets, HD cameras, Wifi cards for traveling and a set of fully integrated cloud-apps to every employee. It wasn’t cheap but no one wants to work with crappy equipment - especially if you’re in the technology industry. Most importantly we trusted them as free-thinking adults and were very transparent with our business and our decisions from day one. We held a bi-weekly all-company meeting where we shared as much as we could, and in the 252 meetings we had, I only missed 3. If the CEO can’t bother to be there, why should the employees? This is just one example. There is no single action that instills trust and transparency, but rather many combined decisions, processes and actions within all levels of the organization.

Taking care of your team also means supporting them when they decide it’s time to move on. In prior jobs, I experienced founders and CEOs who got upset when employees left for greener pastures. While it’s disappointing to see top talent depart, we’ve made it a point to celebrate and embrace the Appirio Alumni Network. From Facebook to Google to Amazon to dozens of GMs and a half dozen start-up CEOs, Appirians have landed at some pretty amazing places and positions globally, and we’re proud to stay connected to them all. I’m also proud to say we’ve had dozens of “boomerang” employees who came back after experiencing another company. For me, that’s the ultimate vote of confidence.

Not everything about our team building was sunshine and rainbows. One of my biggest regrets as a CEO relates to team, specifically around executive hiring. Approximately every other year, for 10 years, I made at least one bad executive hire which set us back in some way - some further back than others. Boards can and will pressure executive team rotation and outside thinking versus promoting from within. And while companies do need fresh ideas and experience that the existing team might lack, it’s easy to rush a hire and not do enough back channel referencing, overlook a rising star internal candidate, misjudge cultural chemistry or organizational fit. In the future, I will be way more diligent in this area and push back more.

5. Spend >75% of your time with customers.

Last but not least, stay close with your customers. No matter what size or stage a company is in, it’s easy for a founder or CEO to get entrenched in the internal processes, politics and decisions that need to happen day in and day out. Fight against this and make it a goal to spend at least two-thirds of your time with customers or those in your organization who work directly with customers (your sales team, your customer service reps, your retailers, etc.) While your team might be your top priority, any company’s success and survival depends on how well it serves the needs of its current and future customers. If you don’t know what they want, what they hate or what they need, your company won’t be on top for very long.

For some channel-driven companies, the customer might actually be partners. This was true in Appirio’s case and was central to another of my lessons learned at the company. When Appirio was first starting out, we lived at the HQ of Salesforce - our primary partner at the time. We strove to be their best partner. When they needed a demo, we dropped what we were doing to create it. When they needed a customer reference for speaking or PR, we called our customers to make sure they had one. But as they got bigger and we got bigger, it became a more transactional relationship as our executive sponsors moved on or moved positions. Our strategies started to diverge, especially when Keith Block hit the scene at Salesforce as head of sales in 2013. A primary strategic pillar for Keith, who had come from Oracle, was Industries and Verticals but we at Appirio stuck to our horizontal approach for another few years before making the full and formal commitment to shift our investments and go-to-market model. Was this delay crushing in the end? No. We still grew, but could we have grown faster and partnered more deeply had we moved in 2014. I believe so.

Another way to stay close to your customers is to be one yourself. Some people call it “eating your own dog food”, but we always called it “drinking your own champagne.” If we were to be evangelists for cloud computing, we knew Appirio’s own systems, processes and productivity tools needed to be 100% cloud-based. Using the systems that we were implementing at (and in some cases selling to) our customers gave us direct insight into their strengths and limitations. It also turned into a meaningful differentiator. We could show our partners and customers what was possible to be 100% “cloudsourced”, and it also meant our largely remote and mobile teams were not only extremely productive but had higher employee satisfaction as well.

While this isn’t an all inclusive list of the lessons learned as CEO of Appirio (that would be a book, not a blog post), it hopefully captures a bit of the journey so others and my future self remember to stay focused and humble, put your board to work, and keep team and customers (in that order) front of mind in everything you do.