Finding Meaning in Enterprise Software

Anyone that knows me well understands that I’m an odd duck.

Follow my Twitter feed and you’ll read tweets about:

  • Customer Success (or rather #customersuccess)
  • SaaS learnings
  • Company culture


But most bizarrely:

Needless to say, I have a thirsty and wandering mind.

On the surface, enterprise software isn’t much of a quencher of curiosity.  We’re not curing cancer or saving the children. We’re not helping humanity get to Mars. We’re not even building a better Emoji keyboard, though the world desperately needs one.

Yet, for some enterprise software employees, the minutiae of the routine is the high in itself:

  • The people that live for the sales gong ringing
  • The people that love “the hunt” for a new customer
  • The people that can tell themselves that every quarter end is “the most important quarter in company history”

What if you’re not in that camp? What if you love your enterprise software job and the challenges but want more?

I’ve wrestled with this a lot personally. If we’re all honest with ourselves, it’s kind of random we are doing whatever we’re doing. I’m the “Customer Success guy” but I wasn’t born stamped with that on my DNA. Different timelines might have me as a doctor, scientist, or (perish the thought) a hedge fund person.

So how can I keep myself motivated? And the same for my team? These are important questions because the cliche about business being a “marathon not a sprint” understates the reality. If you want to build something to last, you need to get comfortable running forever.

In that context, I’ve thought a lot about what motivates me through the slog.


Creating Internal Opportunity


Inside Gainsight, I’m motivated by the idea that our team members can gain responsibility, challenge themselves, increase confidence and build their personal brands. Our head of Marketing, Anthony Kennada, never ran marketing before and has been recognized now as one of the best private company B2B marketers. Our head of Customer Success, Allison Pickens, came from a different background yet she now is recognized as a major thought leader in our industry.

If Gainsight can help people grow in responsibility and challenge, I’m in.


Creating External Opportunity


Opportunity doesn’t stop at our company walls.

I’m energized by the career opportunity that a new job category like Customer Success creates. Post-sales roles were often second-fiddle to sales and product jobs in companies. But as more companies gain more revenue from existing clients (in business models like subscriptions), post-sales (Customer Success) is rocketing up in importance.

It’s energizing seeing this first-hand as we watch Customer Success individuals get promoted and leaders go on to take bigger jobs. Heck – I was even excited when two of our CSMs left Gainsight to take VP jobs elsewhere.

We’ve invested a lot in creating the community around the profession of Customer Success: a big conference, online university, job board, and a lot more.  And my favorite talk track is how Customer Success could be a new pathway to senior leadership – from CSM to CEO.


Doing the Mundane Things Differently


One of the most uninspiring things in life is to feel like you’re living someone else’s script.  And to some extent, the “best practices” nature of enterprise software can make it feel like we’re just going through the motions. For some people, this is great in that they get to take their expertise from job to job.

But I’m inspired by the leaders who look at the routine aspects of business with a fresh set of eyes. Netflix famously said “why do you need expense policies?” Slack’s credits model fundamentally re-wrote the standard “per user, per month” pricing typical in SaaS companies. Atlassian heretically reconsidered the need for salespeople.

At Gainsight, we’re constantly (and somewhat manically) obsessed with getting to first principles.  If another company does sales quotas, product roadmap, or billing a certain way, we love learning from them, but we want to make sure we understand the core logic for the approach. We believe in starting with why and love the “five whys” approach.

Most companies don’t disclose valuation terms to employees. Why? We couldn’t figure it out – so we did. Most companies religiously and almost mindlessly believe that some human beings are anointed from birth as “A-players” and some aren’t. Why? I couldn’t get my head around that. Most CEOs think it’s betrayal for employees to leave them – and treat them as such. Why?  Luckily Reid Hoffman is changing this one.

Thinking Different isn’t just for people making iPhones.


Stroking Creativity


On that note, at Gainsight, I think a lot of us have pent-up creative energy. Maybe we would have been (bad) comedy writers in another life. And I love using Gainsight as an outlet for that.

A few of us in the exec team (especially me and Anthony Kennada) have been particularly passionate about mixing comedy, music, and Customer Success into a bizarre but lovable stew.  And this has resulted in:

But what’s neat is that once you open it up, you can find creativity everywhere. For our most recent Pulse 2016 conference, two of our star teammates, Serra Hetzel and Will Robins, took it upon themselves to write and cast a Disney-inspired musical about Customer Success.

And indeed, while the conference was very well received (56 Net Promoter Score) with some of the most common kudos being for the musical keynotes, we did receive one piece of negative feedback saying “skip the Disney skits and stick to business.” While we respected the person’s point of view, we all agreed that our company runs on this cheesy fun and it’s who we are, so we’re not changing.


Spreading Joy


And to some extent, that’s the thing that’s most motivating thing to me – seeing joyful spirit spread and take on something I never even expected. At our conferences and events, I’m always struck by how much positive energy we see – not just from our staff – but from the attendees (customers and otherwise). One of our company values is “child-like joy” – the idea that everyone has an inner-child inside them full of energy and wonder, and we aspire to bring that to work every day.

I don’t know how it happened, but it feels like child-like joy is spreading into our community, and that’s very satisfying. Customers are making their own videos, and the karaoke section at events is always packed – and there’s always a karaoke section!




To some extent, I wrote this post to myself. I’m hoping to make Gainsight a very long-term endeavor, which means I need to think about how to keep all of us – including me – hydrated with energy and meaning. Hunter Walk talks about this a bit in his post “To Avoid Burnout, Take Pleasure In the Journey, Not Just the Destination.” I don’t know what motivates you in your companies but I do think it’s a healthy exercise to think about it. Unless you’re curing cancer, that is – if you are, just do that and skip the Disney music!

Nick Mehta

As a huge sports fan, Nick thinks of his job as being like that of a head coach. His role is to help bring the right people together on the team and put them in the best position to win for our customers, partners, employees and their families. He’s a big believer in the Golden Rule and we try to apply it as much as we can to bring more compassion to our interactions with others. And he talks way too fast and overuses the word awesome like it’s going out of style. Before coming to Gainsight, Nick was the CEO of awesome leading Software-as-a-Service E-Discovery provider LiveOffice through its acquisition by Symantec and prior to that was a Vice President at VERITAS Software and Symantec Corporation.