Ask A CPO How Do You Take Your Product Upmarket

By Victoria Vessella, Repsly

Growing pains are part of business. If you’re an executive at a software company that’s transitioning away from selling to SMBs and instead trying to attract enterprise accounts, you know there are new set of strategies that must be implemented to meet the needs of a changing customer base.

I recently sat down with Peter Billante, Chief Product Officer at Repsly, who gave insight into how growing companies can gracefully handle the inevitable changes that come with taking your software product upmarket. Prior to his role at the high-growth SaaS company, Billante has held leadership roles in both product and marketing at Autodesk, has led product management at three venture-backed startups that led to strategic acquisitions, and was VP of Product Management at Vela Systems.

There are a host of considerations to think about as your company begins to chase larger clients. Here we’ll explore what the top four issues are, the parties involved in addressing them, and common obstacles to expect.

Tip #1: Work The Roadmap Choosing And Prioritizing Roadmap Themes

“If you don’t know where you are going, any road will get you there.” — Lewis Carroll

A product roadmap is a way companies set expectations, both internally with your development teams and externally customers, when it’s clearly defined and shared at the right time. The themes you choose for your product will probably be different for larger customers, and the order you execute them will be important as well.

For example, larger customers might be much more interested in your product’s ability to provide executive reporting and business intelligence insights; something that might be less important to a smaller customer. In some cases, providing visibility into your roadmap for the next 12 months for large customers may be needed as a sales tool, or so you can coordinate with them on major initiatives

Because your roadmap communicates your company’s vision to potential and current clients, and addresses what problems your product will solve, it helps to setup the conversation for when customers ask for enhancements. Billante explains, “A roadmap can be the lens by which you evaluate customer requests.” That said, not all companies share their roadmaps with customers, but it will still be a useful way to evaluate the input you’re getting from the market.

Tip #2: Find Qualified Partners

“When you need to innovate, you need collaboration.” — Marissa Mayer

Part of taking your company upmarket means working with vendors that can make your base product more sophisticated. With any new initiative, there is a trade off when deciding whether to build your own solution in-house or buying one off the shelf.

However, in cases when the technology is highly specialized or if you need it to scale, choosing to work with a third-party can be your best bet. Today’s SaaS companies in particular can take advantage of hundreds of platforms and tools designed specifically to be embedded into other software products.

There is a myriad of infrastructure partners you might work with, from business intelligence to cloud hosting, foreign language translations, and more. Regardless of vendor type, there are a few tips to consider when deciding about who to partner with:

1. Research, research, research. Read analyst reviews, talk to peers in your network (as they’re likely to give honest insight on working with a given vendor), and look for expert opinions
2. Demo. See for yourself how the partner’s system or platform works and how it can integrate with yours. Your points of contact at this stage are likely to be a salesperson from the partner company, and possibly a technical specialist as well, but often times you can find demos either as videos on the partner site or sometimes even on YouTube.
3. Pilot. This is an integral step in determining if the partner’s product is working the way you need it to and if the partner itself is the right fit for your company. If their solution is a component that is going to be hard to replace, then spending extra time on a pilot is going to reduce risk in the long term.

Tip #3: Expand Your Team

“We hire people who want to make the best things in the world.” — Steve Jobs

A huge part of your company’s evolution to serving an enterprise clientele is staffing accordingly. On the product team front, there are many variables to look at around getting the right fit and they’ll vary from one role to another. Two considerations that come up frequently are a candidate’s industry knowledge and their technical knowledge.

In Billante’s experience, if bringing industry experience in-house is your top priority, hiring from within your customer base can be a great place to start as these folks are both familiar with your product and have the industry chops. Conversely, you might choose to hire someone with a strong technology background on platforms like yours who has a knack for quickly adapting to new industries.

One trend that’s been emerging over the past 10+ years is the rise of the product management function and organization. “Years ago ‘product management’ was often loosely defined, but more recently we see companies of all sizes building out product organizations and hiring multiple product managers.  Universities and business schools are developing more structured programs for product management too, to ready people for the role,” Billante says.

If a big part of the value in your solution is decision making or insights into data, the role of a Data Scientist will become important. Expertise in working with the tools and techniques related to Big Data and machine learning are a must there.

Taking this a step further, Billante tells me machine learning and AI specialists are “one of the hottest roles in the industry today, because there is so much value in it,” especially when you’re working with enterprise customers who can have vast amounts of unstructured data to analyze.

Tip #4: Mind The Gap (In Technical Debt)

“Every once in a while, a new technology, an old problem, and a big idea turn into innovation.” — Dean Kamen

“Many product managers like to focus on new features and leave the existing product in place, but this isn't a sustainable way to operate,” says Billante. “It can work for short periods of time, but eventually your technical debt will catch you.” Making the tradeoff between adding new capabilities while improving the performance and supportability of your current product is something you need to do when you start to go upmarket, and plan for some balancing over time.

It’s a good practice to continuously assess where the greatest need for refactoring of technical debt is based on data that is readily available. Trend analysis in the number of reported bugs and time to fix them are good starting points, or instrumenting the system with a performance monitoring tool can help provide quantitative insights.

Often, system architects or engineering leaders will already have a pretty good hit list too. Addressing the top concerns can often deliver immediate value to customers and could even be a win-win by leapfrogging you ahead to a modern tech stack. It’s possible that an outdated “legacy” part of your system can transform into your newest and best feature with the right approach and investment.

A residual consequence that stems from releasing software updates is delivering them to the customer. Companies have a few options in how they approach this:

• If the project is on the infrastructure side, you may be able to keep the front end of the system virtually identical so that customers don’t know an update occurred
• If it’s a big change in features, you may need to take customers on the journey to the next generation of your product with a thoughtful communication and training strategy
• If you’re able to do a testing and experimenting approach, you may Introduce the updated version of your product in parallel with the old one and let people switch back and forth. Google does this with many products, for example. If your customer’s data is not upgradable to the “Next-gen”, you may need to introduce your new product as a separate version that’s available as an add-on, or potentially licensing both the classic and next-gen for the same price.
• If supportability is degrading, or your underlying platform has an end-of-life, you may need to push all users to the updated system by a selected date

Billante advises that if you know your customer base well, it will help you choose which approach to take. In the case of enterprise clients, companies need to consider the investment level that’s already been made by those who are trained in your product’s current version. Often times those responsible for implementing your solution have documentation and workflows built around it, so it’s critical to keep these key contacts in the loop as your product evolves and give them as much advance notice and runway so they aren’t surprised by a big change coming up too soon for them to prepare.

In Conclusion

Taking your software business upmarket is an initiative that requires new skillsets, processes, and partners. Staying focused in your planning and keeping lines of communication with team members and external parties open are both paramount for designing and delivering a product that is valuable to enterprise customers.

About The Author

Victoria is a Marketing Associate at Repsly, where she works on creating out-of-the-box content for the blog and social media. You also can catch her organizing awesome brand-forward events. A New England native, Victoria has spent time living in Italy and traveling throughout Europe before settling back in Boston. When she's not planning her next trip, V is probably tasting wine or writing for her blog, VixVibes.