5 Tips for Successful SaaS Releases

Phil Britt

Updated · Jul 27, 2015

By Nick Mehta, Gainsight

“Move fast and break things.” By now everyone knows Mark Zuckerberg’s famous words, which were eternalized in the Facebook S-1 and which represent the ethos of a number of the great consumer Internet businesses. Many Web companies like Facebook release daily — even if it means breaking things from time to time.

With the consumerization of IT, many enterprise technology businesses aspire to move with the agility, speed and customer focus of the companies you read about in the tech blogs.

This is easier said than done.

Software-as-a-service (SaaS) speed and iteration aren’t just about fueling development teams with more pizza and tighter timelines. You can implement scrum and daily stand-ups to your heart’s content, but you still have to face a difficult challenge: your customer.

Every customer wants new features and innovation “yesterday.” However, as you scale up and start dealing with larger enterprise customers, they add a new stakeholder to your mix: their IT departments.

At my last SaaS company we closed a multi-million dollar contract with a Fortune 500 shipping company, our largest deal ever. During the RFP process, they were very focused on our roadmap, pushing us hard to commit to dozens of new features — which all made sense, but it was aggressive.

Yet when we finally went live and started our rollout process, they wanted six months’ advance notice and testing time with any new functionality. They were used to a world in which they could get Windows 2000 and deploy it by 2010. Case in point: Their users were still on Internet Explorer 6, which had already been end-of-lifed.

At first, we laughed and made our snarky internal jokes. Then when we learned what the client had to deal with — users in Asia, users in factories, users on slow links, users who didn’t speak English, users on Internet Explorer 6. We gained empathy for their world.

Add to that clients with different configurations, integrations between your systems and those of third parties, global data centers and release management, and a headache is not too far behind.

It’s easy to say, “That sounds hard, forget it; I only want to sell to people who are hip and with it and have the new pre-release iPhone and understand the hack to check their Uber rider score.” If that’s your strategy, more power to you and my condolences to your total addressable market (TAM).

SaaS Release Strategy: You Need One

If you want to meet enterprise customers where they are, having a release strategy is a non-trivial and rarely discussed issue in SaaS.

Indeed, as you grow, it’s a huge challenge to even keep your internal customer-facing teams (customer success management, services, support, etc.) up to speed on the latest and greatest innovations from product, let alone the logistical challenges of keeping videos and documentation up to date.

Release every day like Facebook, and you will most certainly:

  • Piss off your enterprise stakeholders
  • Confuse your users
  • Frustrate your internal team

At the same time, a 12-month or longer release cycle will:

  • Destroy your ability to innovate
  • Create huge holes for your competitors to attack
  • Eventually cause your developers to quit since they can’t “ship code”
  • Piss off your enterprise stakeholders
  • Confuse your users
  • Frustrate your internal team

Darned if you do, darned if you don’t.

Is there a magic answer? As I run my second SaaS business and see these issues again, like I’m living Groundhog Day, I believe there are no easy answers. However, I have a found a few general principles to be helpful:

Be Calendar-driven

I love the predictability of saying “we release on this night of the week/month/quarter” and making sure everyone knows that internally and externally. So if a big feature isn’t ready, it waits until the next release. This is not easy to get used to, but if you have a monthly or greater frequency, the wait time isn’t too bad. Being calendar driven allows all the internal folks and customer groups to plan around your upcoming release.


It’s heretic to support multiple versions in SaaS, but it is healthy to have “preview” releases, even if they are internal. Ideally, if you have a fixed “release to customers” date, you can have a fixed preview any number of days or weeks beforehand.

Documentation Waterfall

Companies often create false choices like “either we can have really complete documentation at release and have a longer release cycle” OR “we can have sub-par documentation.” I’ve found success in approaching this issue like a waterfall: Light documentation at release (e.g., release notes), followed by a rolling thunder of documentation in the following weeks (videos, best practice blogs and more).

Great Announcement Copy

Companies put so much polish into their pre-sales marketing content, yet they treat their release announcements like they were bug reports. Here’s a list of new JIRA items in the latest release. Yay!? Think like a customer would: Why should they care? What are the most important things for them to know? Try this simple test: Would one of your sales reps forward one of your release emails to a prospect to show your innovation? If not, it’s not good enough.

Cross-functional Team

Another Groundhog Day cycle: As your company grows, you will hear various constituencies saying, “I didn’t know about this element of the release.” Consider having a great leader run a regular “release readiness meeting,” where every item of the release is discussed in detail, and where everyone who needs to know does know. This initiative is all about the strength of that leader.

As IT implementation becomes more complex, especially as you approach enterprise customers, having a smart release policy will help you maintain laser-beam focus on the customer’s needs while continuing to innovate. The result: All stakeholders will be happy.

Nick Mehta is CEO of Gainsight, which offers a customer success management platform that leverages customer intelligence and automation to proactively manage retention, reduce unexpected churn and identify up-sell opportunities. Before leading Gainsight, Nick was the CEO of software-as-a-service e-discovery provider LiveOffice, and he was responsible for its 2012 acquisition by Symantec Corporation. Nick also served for nearly a year as an executive-in-residence at Accel Partners, and prior to that, he was a vice president at VERITAS Software and Symantec. A finalist of Ernst & Young “Entrepreneur of the Year” in 2010 and 2011, he participates in the Young Presidents’ Organization, a peer network of chief executives and business leaders. He holds a bachelor’s degree in biochemistry and a master’s degree in computer science from Harvard University.

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