How we pulled off a team-wide demo tournament and what we learned in the process.

August 24, 2022
4 mins

Trustpage is a fully distributed team, but that doesn’t stop us from getting together to have some fun.

Our most recent team outing was a weeks-long, virtual demo tournament where an intense bracket pitted managers against direct reports, engineers against the customer success team, and every combination in between. With our sales team as the judges, each member of the Trustpage team had 10 minutes to run a demo pitching to an audience of buyers representing the personas that the sales team faces on a daily basis.

Our team shared countless smiles and a whole lot of laughs during the process, and we even crowned a winner. But the biggest takeaway? We’re finishing out the year with a renewed focus on our solving our customers problems, because of the hours we just spent talking about them.

Why’d we do a demo tournament, anyway?

In a world where your team lives in five states across every US timezone, its easy for face-to-face time to be focused primarily on getting sh*t done. In the spirit of team-bonding, we wanted to carve out a significant portion of time each week for six weeks to spend time together without talking about deliverables or taking meeting notes.

We wanted to spend time getting to know one-another better: the way we think, the way we speak, the things we value. But we also wanted to spend our time having conversations that added to the value of the business.

When I was considering what our team-bonding should entail this summer, I wanted to design an event that would bring us closer together as individuals, but also help us better understand the way our teams operate and talk about the product so we could leave the event more aligned as a business.

- Emilie, Chief of Staff

How’d we pull it off?

The event-planning was relatively straight-forward for our Chief of Staff to undertake. We hosted the tournament on Zoom, and our Sales team acted as the judges in each breakout room. The following was our process to knock it out of the park:

Set up a bracket

We found a bracket online and assigned the match-ups at random. Our newest employees were granted a by-week, so they could watch a few rounds of demos before competing against our seasoned vets.

Select companies and personas

For each round of the bracket, we selected a company, type of demo, and persona within our ICP. This upped the steaks, and created a more realistic demo environment. Some of the companies we selected were already in talks with our sales team, and some were our own vendors. With each demo, the audience took on the ICP role as their own, challenging our demo-ers with questions each persona might ask during a live demo.

The persona varied week by week, from CISO to CTO to Director of Sales. The source of the demo request also changed weekly, allowing our team to adapt their talk track based on the stage of the call and the prior knowledge of the persona.

Schedule the time

We carved out an hour each week between regular meetings to spend on the demo tournament. Stretched across five weeks, we ended up with some loads of extra team bonding time, but not so much that our schedules were packed.

Execute on the event

The scoring methodology remained the same throughout each round of the tournament—sales-team members issued a score from one to five based on their impression of the demo.

1️ being “I would run the other way after this demo”

5️ being “I need to buy Trustpage right now”

We used breakout rooms to split the team in half, so two folks could demo at once. Each breakout room selected a small portion of the audience to be engaged customers, and the rest of the team acted as audience members. Each breakout room had a designated sales team member to co-sell alongside.

The Results

Each member of the team was able to execute a realistic pitch to a tough prospective customer who met them with interruptions, questions, and objections along the way. From brand-new talk tracks to honing in on the specifics of our value proposition, watching each team member grow and learn as they pitched the product we all work on each day was truly a joy.

New talk tracks

My favorite moment of the demo tournament was watching an engineer on our team implement a brand-new talk track for our demo journey. He tactfully took the theme of our most recent webinar and used this theme as his narrative for the flow. He was not only able to demonstrate the true value of the product, but he wove in a new way to connect the value to the business impact.

- Mara, Dir. of PLS

A customer-centric engineering team

Learned about this future idea for the extension to show accuracy of an answer and from where that answer was taken. Ivan showed this during his demos.

- Andres, Sr. Full-Stack Engineer

It made me more customer-focused. I'm now engineering with a "customer-first" mentality. I also am more empathetic to the job of our sales team and would love to help them out at any point! Tag me in, Mara!

- Kevin, Sr. Data Engineer

I’m always thinking about customers and how they use our product but being required to deliver demo helps me think more about the complete customer story and how they use a feature form start to finish.

- Ivan, Dir. of Product Engineering

A renewed focus on our value proposition

I learned about the different value props for different stakeholders. Our product is useful to Security, Legal, and Revenue teams, and each team gets different, yet related, value from Trustpage. The use case for Legal teams in particular was interesting, because I was not as aware of the major pains that they face.

- Adam, Sr. Full-Stack Engineer

That each buyer of a TC is different and has different needs. It's important to emphasize different features to meet those needs. It was nice to square away the features I was unfamiliar with with the needs of each buyer.

- Kevin, Sr. Data Engineer

I have a better understanding of our different customer/user profiles and the associated value props. As I build the product, I can keep these value props in mind to create the best features possible. For example, Revenue teams rely heavily on CRMs, so making our product integrate easily with CRMs provides a lot of value for those customers.

- Adam, Sr. Full-Stack Engineer

We had a blast learning to more effectively pitch our product and connect more deeply with our customer needs as a team. Interested in seeing what we learned come to live? Request a demo with our sales team to get the scoop:


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