Written by Jared Schachter while working remotely in Costa Rica
We build things that solve problems for digital nomads and remote teams. The borderless products we want to create usually don’t have existing structures, — like health insurance that works the same across countries. Local healthcare options were too restrictive, so we had to create our own structure. Our own social safety net.
Nomad Insurance & Remote Health are just the first steps to a global passport that will provide equal opportunities
to all.
Why do we do this?
The boldness of our mission is what motivates us.
It also means we need a system in place to break down this journey into tangible, manageable steps.
While we keep upgrading our first two products, we have to focus on the next pieces of the global safety net. This includes global retirement and pension plans, disability insurance, parental leave, extended health and life insurance, income stabilization for freelancers, and more.
A key part of the roadmapping process is to generate some excitement for our team and our community while getting us one step closer to our mission.
Why is this process important?
Focus: When we have goals in place, we can easily coordinate efforts around the most important things and truly implement the 80/20 rule to progress faster.
Progress: If we know what we’re working towards, we can measure it. That’s going to get us to our bigger goals faster since we can iterate along the way.
Chance of success: Simply writing goals down makes you 20% more likely to achieve them. With a vision as big as ours and the difficult road ahead, I’ll take any boost in our chances of success.
As we jump into setting goals for the next year, I also remind our team of how far we’ve come, recounting the previous year’s wins to set goals in the context of a longer march rather than a single sprint.
How we set goals
Our entire team decides what we work on next. We use a version of the Objective & Key Result (OKR) framework:
Goal: What you want to achieve.
Measurable: How you will measure your progress.
Unit: The tactical thing you will measure.
We also use the SMART framework when defining a goal, which helps us figure out our measurables and our units:
Specific: Direct, detailed, and understandable
Measurable: It’s something we can actually measure
Attainable: ~50%+ chance of success
Relevant: Makes a difference to our mission
Time-bound: Clear time frame
Our team is divided into “nests” representing a product or function - e.g. Nomad Insurance nest, Remote Health nest, etc. We have company goals, and then each nest has its own goals and timeline that play into the overall mission.
How we plan & prioritize
Our planning & prioritization meetings allow everyone to share their ideas. In the end, it's a democratic, collaborative effort to form the foundation of goals to come.
In addition to our annual goals, we also set quarterly goals so we can iterate a few times over the year and prioritize based on market impact, community demand, and team excitement.
Most companies set goals from the top down. We like to start by engaging all members of the team first - we find this creates more excitement, ownership, and buy-in for the final result.
Here is the typical first step:
The grounding question: What do we want to build? What is needed by our community?
Brainstorming: Everyone on the team does solo brainstorming, writing down their ideas for company goals.
Full group discussion: Then we gather as a group and remove duplicates to create a big list of potential ideas we want to work on.
Prioritize: Once all the ideas are collected, we each rank them based on the expected impact a particular idea will have for our customers and the excitement of team members for the project.
If you want to try this with your team, here’s our template! Write the goals so everyone understands them, and make sure to have a clear idea of how you will measure them.
After the meeting, founders and team leaders go through the ranked ideas and create the company-wide goals for the year.
How we make it happen
Setting goals is just the start. Creating actionable plans for how to achieve them is more important.
Here are some action planning tips I’ve shared with our team in the past:
Write your goal.
Then write all the steps you can think of needed to reach it. All the steps have to be actionable.
Prioritize what needs to happen first.
Create a timeline that shows each step.
To stay on track and jump in if anyone needs help, we update the team on our progress and potential roadblocks once a month.
How we stay on course
Our roadmap is updated quarterly and is informed by and in service of our yearly goals. It sounds easy to say, but it takes discipline to say no to other valuable and cool projects to focus on the goals we’ve already set.
Reviewing the roadmap once every quarter gives us the time we need to build things while regularly responding to ever-changing market needs. It gives us more leeway to scrap things that don’t work (since it’s only three months of effort, we don’t get stuck in the sunk costs trap).
Everyone plays an important role
When we discuss individual goals as a team, it helps everyone connect to the mission and shows exactly how everyone’s effort contributes to achieving it. Yes, some people in the team contribute to the mission more directly than others, but everyone’s ideas and skill set matter.
After the goals are linked to individual contributors, team leads are in charge of surveying progress toward monthly goals and making sure there are no roadblocks. This way, everyone knows what the teams are working on every quarter, which allows us to help each other and brainstorm the best solutions for a particular challenge we’re trying to solve.
Building a new world
Our roadmapping process is not complicated. All we really need to do is listen to our community’s needs and the biggest pain points that need solving. We dream of a better, more equal world and dare to work together to build it.
Our core focus is ensuring that our team and community are involved throughout the process. It stems from the same belief that pushed us to make our roadmap public in the first place: the group is smarter than the individual, when the group has the right processes in place.
Jared Schachter
COO at SafetyWing
With a wide-ranging background in Product & Operations, Jared is making sure that the collaboration in our fully remote team at SafetyWing runs smoothly.
Jared Schachter
COO at SafetyWing
With a wide-ranging background in Product & Operations, Jared is making sure that the collaboration in our fully remote team at SafetyWing runs smoothly.
