Twelve months of agile startup product development 3/3 – bets and goals

July 19, 2022
Christopher Hugentobler
Christopher Hugentobler
Previously the Product and Design Lead at Bowtie Insurance, Christopher is relentlessly curious about defining problems and building solutions for them. He has worked across APAC and co-founded several ventures.

This is part 3 of a three-part story on my experience leading digital product management and design at Bowtie. Previously we shared the structure at Bowtie we setup to build the team culture we want, and how that fuels action towards our mission. We elaborated on how our squads worked, and covered how we stuck to a lightweight development cycle. In this part, we wrap things up by sharing how everything turns into action.

In case you missed it, you can start from part 1: Bowtie’s desired mission and team culture, or check out part 2: Bowtie’s squads and six-weeks development cycle.

Previously we shared the structure at Bowtie to build the team culture we want, and how that fuels action towards our mission. As a recap, here’s how we set things up.

  1. Small, nearly autonomous, cross-function teams; we just call them squads;
  2. A lightweight six-weeks agile development cycle;
  3. Goal-setting at the squad level, with a living Now-Next-Later roadmap.

In part 2, we explained our decision to form small autonomous cross-function teams called squads. And we started to outline how we implemented a lightweight agile development process with six-week cycles.

  1. Six-week development cycles, two-week cooldowns;
  2. Making bets, not backlogs;
  3. Exercise shaping opportunities for betting.

Now we will cover bets, and goal-setting. Starting off with how do we decide what goes into the next cycle.

Making bets, not backlogs

If you spend too much time grooming and looking at your backlogs, you’re probably not very agile.

For decision making and prioritisation, I think backlogs are pretty useless. I almost never use a backlog to decide what’s important, or what gets built next. Great backlogs should help designers, engineers, and everyone quickly understand incidents and feedback that have already happened. They’re a great knowledge management tool. At best, a good backlog will inform the decision.

If you are deciding what to do based on a backlog, good luck.

At Bowtie, we run a ritual called Betting. We do it in a similar way to the way its described in Shape Up. 2-3 weeks before the start of the next cycle, a planning group collaborates on preparing projects that get taken into a betting meeting. The goal of this group is to use the betting meeting(s) to finalise which projects get bet on in the coming cycle.

This working group consists of a small number of product, design and engineering leaders who have the largest amount of influence in their respective functions.

This process isn’t closed off to the rest of the company. Everything in Bowtie is documented on Notion, so that anyone keen to contribute can do so asynchronously.

This working group also collaborates asynchronously. Depending on progress, calls are scheduled to allow for discussions on priorities, feedbacks, strategy, and resource allocation.

How we made our best every cycle was one of the hardest things to communicate with the company. Between each cycle is a circuit breaker. With the exception of only the most special cases, we don’t do any projects across two cycles. In practice, team members understand that they cannot leave unfinished items within a project to the next cycle. Instead, every cycle we revisit our priorities and resources from scratch. Just because a project was important six weeks ago, doesn’t mean that it will be as important six weeks from now. The circuit breaker forces the team to proactively prepare and plan for each cycle.

Before each cycle, we reset and make our best informed bet for what projects will make the greatest impact towards our objectives, given our limited manpower and resources.

Nobody in Bowtie can ever assume that something is “guaranteed to be shipped in the future”. This forces everyone to frequently revisit the company’s and customers’ goals, and make we’re always doing things that contribute to said goals. (We do make exceptions for projects for B2B customers and long term strategic work.)

Sometimes projects we bet on happen to be at the top of the backlog, but in my experience this rarely happens. Often our team members will find creative ways to address backlogged issues as part of a new project, or during cooldown. We are careful not to become servants of the backlog.

Exercise shaping opportunities for betting

We call the projects that we bet into cycles Opportunities. Shape Up covers some great points on what great shaping looks like. At Bowtie, shaping is an activity that is constantly changing and adapting to the people who are involved in it. That’s because everyone involved in shaping does it on the side, carving out time away from other responsibilities to do it.

Nobody works full-time on shaping at the moment, and we’re still experimenting with whether anyone should.

At Bowtie, a good Opportunity must have a very clearly defined set of problems that we think must be solved. Usually these problems are closely associated with a target audience who is experiencing them. To frame the problems, team members can consult metrics that measure user behaviour, or qualitative sources like reviews, call logs, and interviews. Often, team members may need to rely on the expertise of other company stakeholders to fully understand the problems.

Since there’s no formal Opportunities backlog, someone in the betting working group or the wider team usually proposes an Opportunity based on their personal observations of these product feedback loops.

When an Opportunity has its problems laid out, they are lightly prioritised based on their relevance to the squad’s goals and the roadmap. Really good Opportunities will then go further and include potential solutions to the problems. Shape Up does a great job suggesting ways to present potential solutions that help the betting process.

Ideally, we can take enough good Opportunities and a couple great ones into the betting process. This way, the betting working group can have critical conversations comparing which Opportunities have a greater chance of achieving our goals. In addition to problems and possible solutions, here are some optional items that team members frequently include in Opportunities:

  • Future press release;
  • Draft business model, revenue estimate or pricing;
  • Target audience, and how to reach them;
  • Competitive solutions, our unique advantages;
  • Success criteria, measurable goals;
  • Existing solution gaps, blockers, risks.

In reality, we have struggled with managing more than one really polished Opportunity per squad during the time I was at Bowtie. There are several reasons for this that the team is eagerly trying to address.

As mentioned, shaping Opportunities is not a full-time thing for everyone. Alongside day-to-day work, we just don’t spend enough time on shaping. I think this is reflected by the fact that we often have a pretty sense of what problems to solve, but we almost never have enough research done into the insights that we’ve collected, or potential solutions before putting solutions into production.

For leaders, finding capable teammates who want to take up shaping opportunities, and who have the skills to do so, is an incredible challenge.

At Bowtie, these individuals need not be product managers. Others can take up the responsibility of shaping Opportunities too. I personally enjoyed greatly working with Karl, a charismatic engineer who could rally the team behind Opportunities that he believed in, and do an amazing job in bringing the solutions to life.

In summary, Opportunities have clearly defined problems, and some possible solutions. As mentioned above, after betting is complete, squad members have 1 to 2 weeks at the start of each cycle to narrow the scope further, and determine the solution that they will pursue and ship by end of cycle.

In this format, we achieve the desired amount of agility during both betting, and in-cycle design and development. Just the right amount of influence from the right place. Just the right amount of ownership for the right people.

With the unending support of Bowtie’s sales and business development teammates, we managed to keep the cycle compatible with external deadlines as well. Projects for delivering enterprise contracts, and partnership collaterals are also bet into cycle. Due to the nature of the cycle, not everything that sales team wants gets built exactly as requested. But another way of looking at it is we are only ever building what’s absolutely needed and going to move the needle. This type of collaboration and compromise wouldn’t be possible without a huge amount of team-wide trust.

Goal-setting at the squad level, with a living Now-Next-Later roadmap

Our squad members are now enjoying a relatively high level of autonomy. At the start of each cycle, they pick up the Opportunities that have been bet, and they determine the most important problems to solve, and how to solve them. In close collaboration with squad teammates, and sometimes with stakeholders from other teams, they design, develop, test and ship new products and features to customers.

At the end of each cycle, we retro areas of improvement, and try our best to do better next round.

But there’s still one piece missing.

How do our Opportunities, and by relation what our squads are working on, relate back to Bowtie’s bigger picture mission and direction? How do we know that the Opportunities we are betting and working on, contribute to getting closer to our desired outcomes?

As a product leader, it was my responsibility to define these product outcomes, and the way we measure our progress towards these outcomes. At Bowtie, we use OKRs to connect squad activities with company direction. Each squad gets its own set of OKRs.

We have found the best way to set squad OKRs.

Just kidding. I don’t believe there’s one best way to set OKRs. But I do think there’s a couple things worth mentioning that shouldn’t be done.

A common mistake that startup founders and managers make is treating revenue as everybody’s primary OKR. For example, the objective is to grow revenue, and we’ll measure it by number of customers multiplied by the average revenue per customer. Revenue, top-line growth, profitability etc. - these business metrics are obviously important, but they are lagging indicators.

Lagging indicators are inappropriate for squad OKRs. Instead, leaders must brainstorm what are the inputs, that when improved will result in lagging indicator improvements. These inputs are what define squad OKRs, or product goal-setting for that matter.

Another common misconception is to try to make squad OKRs not overlap with each other. The fear is that there would be too many cooks in the kitchen, or the impact can’t be attributed to a specific project or team. My view is that making squads as autonomous as possible already solves this issue.

The biggest challenge for any product leader is to lead and facilitate a conversation among company leaders, to agree on what are the inputs that absolutely require investment by the digital design and engineering team to fix. It’s a delicate balancing act of resource management. And these decisions are reflected by what did and did not get written into the squad OKRs.

At Bowtie, the team would re-evaluate whether squad OKRs still made sense after every cycle once the existing version had run for three cycles.

However, leadership will run out of patience before running out of money.

If you told the rest of the company that every 6 weeks we re-prioritise everything, and review OKRs, and don’t maintain a solid backlog, every single team lead would riot. To give leaders and senior team members a clearer set of expectations on what’s coming next, we created and maintain a living Now-Next-Later style roadmap. This internal roadmap, in addition to communicating progress and what’s new, helps build trust in our process letting our people build the product.

Now shows the type of outcomes we are addressing at the moment. Next shows the stuff we are likely to bet on in the next few cycles. While Later are bigger picture ideas related to our mission and direction. These ideas won’t be built any time soon, but their existence on the roadmap helps team members make better short term decisions that line up with likely long term outcomes.

Since the relative timeframes are already bound by the cycle, we found that Now-Next-Later is a sufficient amount of expectation setting on the timeline.

With the company’s trust, the team can do their best work.

Minimum viable product management

Product managers at Bowtie strive to be both highly visible and invisible at the same time.

To support our squad members to make better decisions about how to solve different problems, our guiding principle is to shorten the feedback loop between user and squad member as much as possible. We strive to support initiatives that allow squad members to understand how the stuff they are building is being used by the intended audience.

Whether this is achieved by reported metrics, collated and cleaned user feedback, observed user behaviours, or something else. Our product managers actively seek to not be the messenger of feedback, or to reduce its incidence as much as possible. We strive to shorten the feedback loop between designers, engineers and user needs.

At the same time, product managers remain a highly visible source of direction and truth for all stakeholders. If there’s someone who’s best informed on finding the perfect balance among user needs, business goals, available resources, we hope that our product managers can be trusted to find that balance.

Taking everything mentioned together, here’s a snapshot of everything new that the team shipped in 2021 over 6 six-week cycles. Projects like performance and infrastructure improvements, bug fixes, partner or affiliate campaigns, compliance requests, design and developer operations, internationalisation aren’t included below, but I estimate they took up 15-20% of the team’s available time.

After Cycle 10, the team organised a hackathon and spent a couple weeks working on that and enjoying a well-earned holiday.

Over this time period there was no more than 10-12 staff involved full-time in Bowtie’s squads. This figure has grown since then. Over 2021, we more than tripled our recurring revenue and customer base, while holding churn steady and improving user satisfaction. We launched several new products, and are well positioned to capture market share in both insurance and health. Although we are just getting started, with the Mitsui partnership announced with our Series B, we are one step closer to achieving our mission.

Cycle 5 (2021 first cycle)

  • Company HR managers can better submit accurate company information in group medical application - B2B, Insurance
  • Employees of group medical customers can enrol into more than one plan type per company - B2B, Insurance
  • Custom employee benefits onboarding flow for large enterprise customers - B2B, Health
  • Product renewal on first year anniversary of BowtieGo products - B2C, Health
  • BowtieCash rewards program now available for more products - B2C, Growth
  • “4Protection” landing page campaign - B2C, Growth
  • Education center to guide users how to choose the right type of insurance for themselves - B2C, Growth
  • New individual applicant can better compare product options during the application - B2C, Growth
  • New inputs, lists, interactions and quick actions for underwriting and claims officers in admin panel- B2C, B2B, Operations
  • Launched first version of an instructions service to handle repeating tasks - Operations

Cycle 6

  • Product renewal on first year anniversary of VHIS products - B2C, Insurance
  • Launched first health rider to both new and existing customers, and allow users to redeem health services with BowtiePoints - B2C, Insurance
  • New error handling, lists, interactions for new individual applicants during underwriting - B2C, Growth
  • Members can submit claims for pre-approval by new partnership with third-party administrator (not launched because partnership postponed) - B2C, B2B, Insurance
  • Handle different iterations of insurance products during configuration and claims approval - Insurance, Operations
  • Admins can customise admin panel layout to accelerate personal workflows - Operations
  • Settlement letters are automatically generated and sent to customer - B2C, Insurance, Operations
  • Bowtie anniversary landing page campaign - B2C, Growth
  • Launched new illustration library - Growth

Cycle 7

  • Members can better file claims, find pending claims, view claims status in app - B2C, Insurance
  • Rider customers with active BowtiePoints can activate their services with valid digital vouchers - B2C, Health
  • Launch of Bowtie clinic landing page and generate digital body composition analysis report - B2C, Health
  • Bowtie clinic staff can manage patient data and basic workflows for clinic opening - B2C, Health
  • Launched group medical products with outpatient coverage together with new group insurance webpage - B2B, Insurance
  • Members can submit outpatient claims in app, and they will be processed - B2C, Insurance, Operations
  • Product renewal on first year anniversary of group medical products - B2B, Insurance
  • Claims officer can better find claims documents, review insured life information, and generate reimbursement results - Insurance, Operations
  • Finance officer can better approve and payout claims - Insurance, Operations

Cycle 8

  • Sales can submit and approve discount schemes for individual customers buying group medical plans - B2B, Insurance
  • Admins can create PDF document templates on admin panel to be reused throughout application - Operations
  • Clinic customers can receive digital bodycheck reports and browse a health glossary for guidance - B2C, Health
  • Users are recommended what products to buy together and get personalised premium estimates - B2C, Growth
  • Customers can adjust their sum-assured amount for products that have that option, and certain product restrictions were reduced - B2C, Insurance
  • Customers can find a history of changes made to their in-force policies - B2C, Insurance

Cycle 9

  • Launched first enterprise plan tailor-made to a large customer’s specification - B2B, Insurance
  • Replaced old customer referral program with new program that worked with new products - B2C, Growth
  • User can better understand reasons behind exclusions or premium loading during application - B2C, Insurance
  • Accident insurance underwriting questions reduced by 75% - B2C, Insurance, Operations
  • Users can better discover, retrieve and activate health vouchers in app - B2C, Health
  • “Debug” landing page campaign - B2C, Growth
  • Replaced telemedicine provider with new provider and streamlined flow - B2C, B2B, Health
  • Admins can better create, search, manage health vouchers in batch - Operations
  • Introduced justifications to underwriting decisions - Operations

Cycle 10 (2021 last cycle)

  • Launched Bowtie’s first medical insurance product with full coverage Bowtie Pink - B2C, Insurance
  • Admins can create, edit, test, underwriting question flows for different insurance products and save versions inside admin panel - Operations
  • Users can better submit outpatient claims - B2C, Insurance
  • Users can save payment details to their profile to be reused for claims settlement - B2C, Insurance
  • Preorder page for new experimental health product for parents with kids - B2C, Health
  • Revamped company homepage - Growth

Bowtie is hiring builders to engineering, design, and all roles. It is a hybrid remote company, with teammates distributed in several time-zones. It operates an excellent café and clinic in downtown Hong Kong. Reach out to Sara Choi or I.

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