Webinar: Aligning Product Roadmapping with Company Goal-Setting

Recently, Mainsail Vice President Kate Hopkins hosted a webinar with Mainsail Executive-in-Residence¹, Jeff Gardner (former CEO of Zen Planner), Mainsail Vice President, Phil Stern (former head of growth at Zen Planner) and Matt Share, former director of product at Zen Planner. Zen Planner, a SaaS solution for the fitness industry, was a previous portfolio company of Mainsail Partners.

In our time working with Jeff, Phil and Matt at Zen Planner, we found that the company demonstrated a highly developed and effective approach to strategic planning both at the company and product level. In the webinar we discuss: How to Keep your Product Roadmap Aligned with your Strategic Priorities.

You can watch the entire webinar here. Highlights are relayed below.

Setting a Framework for Annual Strategic Planning

Kate Hopkins: How do you think about your product roadmap as it relates to your strategic company planning?

Jeff Gardner: Product strategy should always follow business strategy. Because software is such an agile business, quarterly goal setting is the best cadence. Your quarterly goals should flow from annual goals.

At Zen Planner, each December, we would go offsite to set annual goals. Then, three weeks before the end of each quarter, we would set our “Big 3” goals, which became our roadmap for the coming quarter. That would flow down to every function and every team member, who would each have their own Big 3 goals, all of which would align back to the company’s Big 3.

Once your goals are set, it is critical to have transparency and accountability, with your teams regularly reporting on progress and learnings. At Zen Planner, we had weekly team touch-bases that covered our progress. Additionally, every individual had a weekly 1:1 with their manager. In every meeting, we referenced the Big 3.

Kate: What is the right level of a goal?

Jeff: Software companies need to set aggressive, achievable and bite-sized goals. At the executive level, that means setting thematic goals. Then, leave it up to each function to assign specific goals and metrics.

Setting quarterly priorities

Kate: At the beginning of the quarter, how do you come up with the Big 3 for each team?

Phil Stern: As a sales team, we would start by reviewing the company’s annual and quarterly objectives. Then, we’d set our team’s goals, aligned to those. Every functional group underwent this same process.

Kate: How did these goals break down for product ROI?

Matt Share: This is the fun part. With the company’s annual goals as guardrails, the product team could begin research and discovery. We ask ourselves: what can I deliver to influence the objective the company is trying to hit? With various hypotheses in hand, we get together, present our ideas, and debate.

What are the pros and cons of prioritizing various features? Which will help us hit the goals? Why? What research proves that?

Kate: You can’t do everything on this list, so how do you decide what to prioritize?

Jeff: Every product team starts with a massive list and then meets with Sales, Customer Success, and others to understand what is going to bubble to the top that quarter. These conversations must be completed before you start scoping projects. Too many companies waste resources scoping products they will never be able to build.

Executing against the quarterly plan

Kate: After your goal-setting meeting, there’s a lot of work to do. How do you align the roadmap to your sales goals?

Phil: We took seriously our responsibility to know our customer. So, if I defended the need to build one function over another, it came from informed discussions, backed by data. We all thought outside of our functional cycles and that made it easier to support the roadmap. It makes it easier to give up something you want for a function you believe will have a greater impact on another part of the company.

Kate: How do you narrow your product roadmap down to the final list?

Jeff: Product and Sales partnered on this for months. They completed competitive research. When we were planning our launch into yoga they spent time on-site with customers (including taking yoga classes!). By the time our GTM strategy came out, it was clear which features would serve our success.

Kate: What were the social and team dynamics of these product tradeoffs? How did you make those decisions and still pull together as a team?

Jeff: It’s all about sharing a mindset that you want to create the best product possible. In our planning meetings, we would have full-on debates. Someone who didn’t know us might even call them arguments. But we would walk out of those meetings with our arms around each other because we knew we had come to the best decision for the product. We checked our egos at the door.

Kate: What about bugs? How do you balance forward momentum with the reality of needing to fix bugs?

Matt: Of your true total development velocity, less than 20-30% should be bugs. Knowing that, we allocate a percentage of our scope to things like security and bugs, so it’s expected to be part of the development process.

Kate: How do you balance investing in most-used product offering and expanding your audience?

Matt: Your company’s goals should set your priorities to answer that question for you. If the product team can be informed enough to act with that “founder mindset”, they can bring suggestions on how to approach product development that aligns.

Jeff: As CEO, I will always push toward building and creating more. With that, you will always create bugs and technical debt. One quarter, we just stopped and spent time cleaning things up that could have created bigger problems. That was part of our strategy, too.

Accountability for quarterly progress

Kate: How do you determine the metrics to hold yourself to for the rest of the quarter?

Matt: Coming out of quarterly product planning meeting, I would go back with the Product Managers to our Scrum team for another kick-off meeting. We would present the company’s annual goals, the research we completed and the roadmap we decided would be most impactful for those goals. Then, with that context, the engineers and development team would set reasonable and aggressive goals with specific analytics.

It’s motivating for your engineers to be a part of the greater conversation. Innovation can come when your engineers know context for the company.

Kate: Over the course of the quarter, how do you track success?

Matt: We are always measuring standard usage metrics. Then, we’re targeting the specifics of those metrics based on the initiative we’re focusing on that quarter. We measure everything monthly, some weekly, with checkpoints built in. We highlight what’s not working and we adjust.

Kate: Roadmaps have a tendency to expand. So — how do you balance between expansions and sticking to commitment?

Jeff: Believe it or not, we had quarters in which we achieved everything on our roadmap! We were clear about what we wanted to build this quarter and we had an ongoing list for the future, so we could always push things down the line. That’s why regular check-ins are important — to verify if things are getting done when you thought they could.

Matt: To add to that — it’s important to celebrate when your estimate is accurate. When it’s not, your engineers shouldn’t get punished, because that encourages them to skip steps in the future. Rather, ask what you learned about how long the process took. The point of estimating is to get good at estimating. Emphasize learning and accuracy, not speed.

Kate: How do you stay on track if you get approached by an enterprise opportunity?

Phil: We were cautious to adjust our roadmap, even for a partner at that scale. We agreed that we were doing this for the best possible experience for our entire customer base, not just the biggest customers. If an enterprise client had an idea for a function, I had to prove it had applicability to the entire base before implementing it. We probably turned down 95% of those requests, in favor of our existing customers.