Octopus-branded security badge with text that says Bob Walker, Technical Director of Customer Success, above the silhouette of a man wearing glasses.

At the helm with Bob Walker

Bob Walker

This post is the next in our series, chatting to people at Octopus about their role, what they’re working on to improve the product for our customers, and more.

Here we talk to Bob Walker, our Technical Director of Customer Success.

How long have you been at Octopus and what drew you to work here?

I was using Octopus Deploy before I joined Octopus. I saw first-hand the benefits of implementing Octopus Deploy at 2 different companies.

Before using Octopus at these organizations, we deployed major releases once per quarter, and it took several hours. The deployments required emergency fixes for days after. It was easy to miss a database change or forget to update a configuration file.

After implementing Octopus, we deployed every 10 days, and it took 15 minutes with no emergency fixes (outside of missed bugs).

Being a user and a fan, I followed Octopus on Twitter. In late 2017, I saw they were hiring in the US for the role of pre-sales engineer. The chance to work in CI/CD and help customers use a tool I loved - sold! I applied that night.

Fun fact: I filled out some forms on my first day then boarded a plane to Brisbane, Australia. Ryan Rousseau, Principal Solutions Architect, was hired on the same day, and we were the first 2 US-based employees. The onboarding infrastructure we have today didn’t exist, so onboarding had to happen in Australia.

What does the Customer Success team do?

We do what it says on the tin; we help our customers be successful after they purchase their license. Success takes many forms and requires different areas of expertise. We have:

  • Customer success managers and account managers building relationships with our customers
  • Technical account managers helping our customers get the most out of their license
  • Solutions architects helping overcome technical challenges
  • Licensing and renewal specialists answering those tricky licensing questions
  • Sales operations and training staff keeping everything running smoothly

What does a typical day look like as Technical Director of Customer Success?

As mentioned, I was one of the first US-based employees at Octopus. I woke up each day for the first few years with the simple goal of determining how best I could help customers. I wore many hats and performed different tasks. I answered support tickets, wrote blog posts, hosted webinars to show off new features, and helped customers 1:1 to overcome roadblocks.

My day-to-day now focuses on leveraging my experience and perspective to support everyone in the Customer Success team. I might walk through bursting scenarios with a new customer success manager; share knowledge about the history of our product with the solutions architects and technical account managers so they can better help their customers; provide feedback to our Product team so they have the context to determine our next focus; ensure everyone knows about new features and functionality.

What are the most common questions from our customers?

Our questions vary each week and with each release.

We recently released 2022.1, so we’re getting lots of questions about how best to use Config as Code.

When we get similar questions on a topic, you’ll see us update our docs or add new examples on our public samples instance.

We received lots of questions about upgrades a while ago, so we re-wrote the upgrade guide to include topics our customers were asking about. Late last year, we addressed the need for rollback examples by creating a new space in our samples instance and hosting a webinar to demonstrate rolling back.

How does your team keep up with all the changes in the world of software and our ever-evolving product?

We stay on top of our game with "sharpening time". Sharpening comes from a quote attributed to Abraham Lincoln:

If I had six hours to chop down a tree, I’d spend four sharpening the axe.

We encourage the team to sharpen their axe by diving into a topic that interests them or a feature we're releasing next quarter.

The great thing about unstructured sharpening time is that you don’t know where it will lead.

For example, Shawn deep-dived into Kubernetes and set up his cluster running on Raspberry Pis. Meanwhile, Adam deep-dived into AWS and configured the team’s VPCs, Subnets, IAM, and anything else shared. Before releasing Config as Code, I spent time poking around the edges to see what we're supporting and not supporting.

How do you measure success internally and for our customers?

It’s tricky to isolate one metric to measure success for our customers, as each person uses Octopus differently. A SaaS company that creates a unique infrastructure per customer faces different challenges than an insurance company with a suite of internal-only applications.

Ultimately, we want our customers to be happy and successful using Octopus Deploy. One way we measure success is by looking at renewal and expansion percentages. But that’s not the only metric. I’d hate for someone to renew their license “in anger”. We evaluate a host of other indicators, such as duplicate questions, number of questions, version use, feature use, and more.