Help wanted

As is true for most early stage founders, wearing multiple hats is just part of the job. I scheduled demos and closed deals, onboarded new users myself, and became their personal account manager whenever they had questions.

I was also the support team. Any time that someone had an issue, or worse, when something broke… my inbox would light up with angry emails.

After surpassing a few hundred active users, we graduated from my inbox to Zendesk. I held down the fort solo for over a year until I got an email from one of our users, Darwin.

He was a power user of ours and after going back and forth on tickets for months, he eventually reached out and expressed interest in joining the team.

It was nice to have some help, but those were the dark days for support (and my sanity). Darwin and I would routinely be up past midnight slugging our way through the support queues.

Even when I went to Oktoberfest in 2022, I would come back drunk from the beer tents and answer support tickets for hours on end. Provided damn good support too.

Sober or not, it didn’t matter — replying to tickets was second nature to me and it was just the name of the game at the time. I knew the platform inside and out.

Despite wearing that as a badge of honor, it wasn’t sustainable.

After raising our $12.5M Series A in the spring of 2023, it was time to scale the team a bit. We hired Jess then Beth then Tina, built out some support processes and macros, and ended up forming something that actually resembled a real support team.

The goal was to transition support from a safety net to a true value-add service. In my mind, support presented an opportunity to build a deeper relationship with our users.

2024 was a massive year of growth for us:

• We entered the year with a few thousand users sending 750M emails per month.

• Currently servicing over 20,000 active users sending nearly 2B emails per month.

Not only did our user base grow a ton, but so did the complexity of the app.

So 10x the users, 10x the complexity… and naturally you’ll end up with tons of support tickets. To maintain the same timeliness and quality of support, we began hiring pretty aggressively to meet that demand. Before long, support quickly became one of the largest teams at the company.

It’s not just a cost thing. Each time we had to scale the team there were a ton of second order effects to consider:

• Each open role required existing employees to interview, vet, and discuss the candidates in the pipeline.

• Each successful hire required additional rounds of onboarding and training.

• Constantly scaling the size of the team required new processes, managers, and meetings.

We were on this hiring flywheel for most of 2024. So as a founder, what do you do?

As a first step, you try to prevent the influx of support tickets. In most cases, a user submitting a support ticket indicates that they ran into some sort of issue and need additional guidance.

An oversimplification: support tickets = bad user experiences.

I created a hierarchy of initiatives to prioritize in parallel to hiring. The goal was to provide a far greater experience for our users and flip this hiring flywheel on its head.

1. Platform: Improve the performance and intuitiveness of the platform to reduce confusion and errors.

2. Resources: Create a diverse ecosystem of resources to empower users to resolve issues on their own.

3. AI: Provide always-on escalation paths that optimize for speed.

4. Support: Fallback to our support staff for matters that require more technical and strategic intervention.

For the past year or so we have been relentlessly pushing these initiatives forward. Here’s how 👇

Platform

• Hired 2 incredible product designers to craft beautiful and intuitive user experiences.

• Dedicated a 6-week sprint to squashing all of the most commonly reported bugs and improved the experiences which led to the most support tickets.

• Rebuilt our entire data infrastructure layer to be far more performant and provide event-based data in real-time.

Resources

• Hired someone full-time to create and update dozens of support articles each week.

• Launched a brand new knowledge base that is easily searchable and packed with value.

• Publish a handful of video tutorials each week to our YouTube channel.

• Publish at least 10 articles per week to our blog to educate users on best practices.

• Launched a beautiful new Help Page to aggregate all of these resources in a single place.

AI

• We have been building and training Buzz, our AI chatbot, to confidently and accurately resolve a wide range of issues in seconds.

• This AI chatbot can resolve most user inquiries and is only getting better with time.

Support

• We have 15 incredible support specialists, each with deep industry expertise and technical skills, to provide hands-on guidance for our users.

But we decided to take it one step further. Just last week we made the decision to only provide “human support” for paying customers. From a business perspective, I’m confident it was the correct decision.

We dug into the data and saw that about ⅓ of our support tickets came from users on the free plan, of which, very few ever ended up upgrading to paid.

Imagine for simplicity’s sake that we’re spending $1M per year in support salaries: that translates to over $300,000 in costs in exchange for essentially no revenue. That’s a losing equation.

By moving this level of support to paid plans only…

• Paying customers will receive far more quality support, much more quickly.

• Free users can still take advantage of our abundant resources and tutorials of which we’ve invested heavily.

• We can scale the company sustainably and get off the hiring flywheel.

Back in my Morning Brew days, we were at one point paying Mailchimp more than $10,000 per month and could only ever speak with a chatbot that sent us outdated support articles.

I’m confident that with our highly technical support staff, we can be a true extension of our users’ teams and help them succeed. I view support as a competitive advantage in this industry, and it’s only going to get even better from here.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/help-wanted

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