Use This Framework to Set Your Startup’s Roadmap

Use This Framework to Set Your Startup’s Roadmap

Use This Framework to Set Your Startup’s Roadmap 1600 900 33Voices

Rewind two decades and Matt Williams is sitting in an advisory meeting, his company LiveBid didn’t have an official board yet, listening to assertion after assertion that he should close down the business. 

It was the late 1990s, and his advisors raised valid points. Matt was paying salaries on credit cards as he attempted to lead his team, a few of them even living with him at this point, through obstacles that the advisors felt were prohibiting the company’s growth. 

Despite their warnings and a make it or break it capital crunch, Matt persisted “to the nth degree” to keep the three-year-old startup alive. 

In May 1999, LiveBid was acquired by Amazon where Matt served in  senior leadership positions for over a decade. 

“It was the craziest thing I’ve ever done,” he shared. 

“It was so meaningful to me in life to have accomplished that in the face of everyone saying not to do it.”

Today, Matt is the Founder and CEO of The simplest way to find home professionals to complete your renovation projects. 


Matt’s deliberate and thoughtful leadership guiding the Seattle-based startup is largely shaped by his experiences at Amazon, Digg, and Andreessen Horowitz, where he spent time as an Entrepreneur in Residence. 

In today’s featured interview, he shares an in-depth look at the goal setting framework fueling the team to serve over 5,500 cities.

“The single biggest question entrepreneurs face is: What’s working, and how long is it going to work for?” 

It’s the tricky dichotomy between persistence and patience; How do you exercise vigilance and speed when walking a tightrope? 

“An operating discipline focused on data and metrics,” Matt explains; Citing one of the chief lessons he learned working under Jeff Bezos at Amazon, which he describes as “the world’s largest startup.” 

Young companies especially need to “measure their businesses relentlessly.”

The only way to achieve this is through a set of clear company goals that involve and inspire each member of your team. 

Every quarter, set one or two large goals that drastically drive your business forward and six to 12 smaller goals to make progress on specific metrics. 

Your high-level goals should result in a “game-changing shift in conversion, customer behavior, or experience.” 

For Matt and the team, these center on the number of home renovation jobs on the platform and revenue. 

To determine your primary quarterly initiatives, ask yourself: 

  • What are the mission-oriented goals we are going after as a company? 
  • What are the key metrics we are trying to impact?

Approach your smaller goals as pilot experiments focused on specific metrics. For example, at, a quarterly project can be reducing customer acquisition costs across markets. 

Depending on the size of the project and your company’s resources, these experiments should be executed and debriefed quickly. 

Generally, you don’t want to spend more than two weeks on a trial. However, projects tested by your sales team, for example, may require a longer timeline due to a physical team making calls. 

The core benefit of this framework resides in your time evaluating each goal. 

Institute everything for immediate measurement.

If you were to walk into a debrief meeting at you’d notice that the evaluation process  is incredibly straightforward. 

Based on Matt’s time at Amazon, the conversations are centered on three questions. 

  • What worked? 
  • What wasn’t successful? 
  • What do the metrics look like? 

Debriefs are about data, questions being asked and answered, and decisions being made on next steps.

In both positive and negative ways, your data will reveal outcomes you didn’t anticipate.

As a company leader, you should be adamant about “determining when to a cut a project and try something new.” 

It’s a mental exercise of letting go. 

“You have to be open as an entrepreneur and a team about the honest reality of what is working,” Matt explains. 

If you can set ego aside and exercise humility in your business and the trials you’re performing, you can build a successful company.

You’ll often find that your team is executing ideas today that you wanted to act on six months, or a year ago. Similarly, ideas you’re currently discussing may not come into fruition until 2017. 

If you remember one thing: Focus on the data.  Your data will tell you when you’re ready. 

As each of these processes simultaneously flow throughout the organization, it’s important to find quiet time to review these goals on your own. 

Matt reviews’s quarterly goals every day. The quiet time is critical to shaping the company’s roadmap and evaluating your team’s performance (both individually and collectively), to ensure that everything is on track.

“Startups are nothing but roadblocks,” Matt explains. 

As a leader, “it’s your job to remove them along the way.”

The most significant way to elevate individual performance is to make it a priority that each team member can confidently answer these two questions.

  • What am I working towards this quarter? 
  • How is my progress being measured against this goal?

Ideally, you want to spend one-on-one time with each team member to help them “architect their own path.”

“In order to be productive, you have to have clarity of goals and mission,” Matt asserts. 

Everyone should come to work every day knowing the metric they’re trying to impact.

It’s wise to institute weekly check-ins with your team to “establish the top things the company needs to accomplish that week and tie those goals to units of progress.” 

At, Matt leads a Monday meeting where the team reviews their goals, accompanying metrics, and the next steps to achieve them.

As you perform each of these experiments your competition will be doing the same. Whether or not their’s are successful, avoid focusing on them in “an unhealthy or reactive way.”

While studying their journey enables you to gain valuable lessons about what works and doesn’t work in the industry, “focusing on your competition doesn’t yield results as much as focusing on your customer.” 

Your customers give you your data. Follow their lead, not your competition’s. 

When analyzing your metrics actively distinguish between customer feedback and behavior. 

It’s one thing for a customer to relay a feature they’d like to see in your product. It’s another for them to actually use it. 

As you test, iterate, and validate experiments “use direct action as feedback.” 

A deliberate and unwavering focus on your customers behavior will enable you to maximize this framework by optimizing for tangible growth in the right places. 

To gain deeper insight into how Matt and the team are achieving this follow him on Twitter at @talktomw and visit the team here