From startup to scale up: how to roadmap - Jen Flynn

From startup to scaleup – how to roadmap – Jen Flynn, Airtasker

0 Flares Twitter 0 Facebook 0 Google+ 0 LinkedIn 0 Email -- 0 Flares ×

Jen Flynn How to roadmap

One of the most important things you can have as a Product Manager is have a good roadmap. It helps your vision, helps your plan and helps you actually know what you’re going to do when you show up in the morning.

Roadmapping is so important for the actual delivery of product improvements and market growth. VP of Product for Airtasker Jen Flynn explains and shares the story of Airtasker’s transition from startup to major player in the online space.

A native of Ireland, Jen’s career covers platforms including Europe’s Truvo, REA Group and Sportsbet, and she’s a pro on deconstructing a vision and creating a roadmap that can be executed efficiently.

How to Roadmap Beyond Product Market Fit – Jen Flynn – Airtasker from Brainmates Pty Limited

About Airtasker

Having proven itself in the marketplace, this on-demand job platform is in the process of transitioning from startup to ‘scaleup’. From humble beginnings with a small crew on board, it is now large enough that users have high expectations. They want a smooth experience with no bugs.
Airtasker was able to scale and expand after achieving initial product market fit by making strategic partnerships. This included electronics outlet ‘The Good Guys’, which had previously been offering a ‘concierge’ service for delivery and installation that was all handled manually at the point of sale.

A second partnership linked Airtasker with SevenWest Media, taking it to the big league and offering excellent media exposure and increased opportunities.

Along the way, Airtasker has learned several lessons. In once instance, an engineer opted to leave, explaining that he enjoyed the less formal feel of a tiny startup. Jen explained that the people who join a startup aren’t the same people who work in corporate.

“They’re innovative and optimistic but as you scale you do need those more corporate behaviours. You need people to build relationships, bring teams together and build connections.”

“While scaling, we realised that you can’t just hope things will be ok. We needed to hit actual benchmarks. This switch can sometimes be difficult for the people who came into the business early.”

Jen explains, “As a PM or product leader, you have to get people to join you on the journey, while understanding from your end that it can be emotional for some of them”.

Finishing the product evolution section of her presentation, Jen discussed the importance of governance and making sure that partnerships won’t affect the balance of the company.

Recently Jen created a goal wall – “if what you’re doing isn’t on the wall, you shouldn’t be doing it.” Three months in and despite initial resistance, “This is starting to work. People are joining the product leads in referring to the visualisation of goals on the wall.”

Finally, Jen explains that in a growing company, authority actually needs to de-volve. The people who started and are at the head of the company may not actually be the ones qualified to make decisions. By the stage Airtasker is at, a company should have a product steering committee and allow Product Managers to be final decision makers in their areas.


Jen asked the Leading the Product conference – has your roadmapping lost its way? “It’s supposed to be a force for good but heads can roll for what’s not delivered. Sometimes there can be outside factors that interfere, resulting in a roadmap that doesn’t achieve its goals”.

This is why, Jen reminds, a roadmap must be living, breathing, not laminated and susceptible to change. What’s more, “Not every roadmap is the same. It needs to support the specific goals and needs of your organisation.”

Two types of roadmap blockers

Jen explains that a roadmap can end up in trouble thanks to a couple of types of people within the company:

The micromanager – people who get stuck in the details. Jen’s advice is to take heed that people who aren’t comfortable won’t make decisions. “Work out what they need to feel comfortable and keep them moving”, shares Jen.

‘See-sweeters – the choose your own adventure / pick ‘n mix people who can’t see all the hard work you have actually been doing and get distracted by the next shiny thing. “If you encounter these people”, says Jen, “find their influencers and get approval from above to stick with the original vision.”

Secret Road Mapping tips for product leaders

“When used well, a roadmap is a powerful tool in a product manager’s arsenal but it’s a living thing”, says Jen. A good roadmap:

  • Needs to be goal oriented, not necessarily project oriented
  • Can, will and MUST change (otherwise you don’t notice industry changes like, for example Facebook)
  • You have to ‘walk the road’ daily so that you know what you’re doing and why
  • Try to get into good habits and encourage your team to do the same

jen flynn
Leading the Product SketchNotes by Rebecca Jackson

About Jen

With previous roles as Head of Product Management at Sportsbet and Head of Product – Residential at REA Group, Jen is now VP of Product at Airtasker.

Jen brings over 15 years of expertise in developing commercially robust business and product models to the digital industry. With a result driven focus, she has guided and motivated multi-disciplined teams in dynamic markets, achieving sustainable growth.

Driving your product management career, Victoria Butt, Parity Consulting

Creating value for customers, Dan Olsen, Author

Outcome driven innovation, Doug Blue, Seek

Details are the difference – Ash Donaldson, Tobias & Tobias

Life after launch – Cameron Adams, Canva