2 years at Postman - Building a lean, outcome-driven, high-performance Strategy and Operations team

A couple of days back, I got a little nostalgic and spent five minutes writing a Twitter thread on my journey in building the Strategy and Operations team at Postman from scratch. After a number of messages from people asking for more specifics, I thought it deserved a longer post. So, here goes!

Some background

I had been following Postman closely since 2018 when I noticed my developer colleagues using the app in my previous role. In 2020, I observed through LinkedIn that the GTM team had grown from 3 to ~20 in the past year but there was no StratOps function. After a sales role at Freshworks and interesting Strategy and Operations projects as a management consultant at Deloitte, the challenge to build a function from scratch in a fast-growing rocketship seemed very interesting.?

I cold-emailed Abhinav (CEO) and Ankit (CTO), with a few slides on what I wanted to accomplish at Postman. After a few conversations with Sanjeev (VP of CS) and some interviews with the leadership, I joined Postman in Nov 2020 as the first hire in the newly created StratOps function.?

The first few months

The first project I started on, the day after I joined, was building the Sales/CS territory model and books of business for 2021. It was the first time this was being done at Postman. It was tough because I didn’t anticipate a lot of challenges that came with doing something of this size for the first time. Some of them were getting the right data from the CRM, analysing and determining the factors on how to create equitable territories for different teams, or learning in parallel how the best companies in the world do it efficiently and lack of time (I had 45 days to wrap this up). I also wanted to learn the product better at this point and joined a lot of calls with Solution Engineers and CSMs.?

Burning midnight oil on the territory model helped me identify a lot of operational gaps in the GTM motion. I realized the scope of things that we could do to make an impact and drive outcomes was vast. It required thinking bigger in terms of execution and making a plan. I ended up writing a 12-page document with a list of goals, projects and outcomes. We hired our first 2 interns in April 2021 to test my hypothesis that the StratOps team could drive these outcomes.?

I have seen a lot of StratOps teams taking up every request that they get and have a lot of backlogs. Operational debt is huge in such cases and people lose focus on outcomes and all work becomes a task. Right from the beginning, my eventual goal was to build an extremely lean team that adds disproportionate value to the GTM Org and Postman because scaling a team linearly with the rapid pace of Postman’s growth was not a sustainable option. It was a tough call because I would have to say no to a lot of requests.?

Hiring and Ramping

Hiring was tough and exhausting because we did not have a framework for the skills required or an interview structure. Also, the hiring pool for a function like StratOps is small. Ultimately, working with the recruiting team and GTM leaders, we decided to go for candidates with good analytical skills, a great attitude, a culture fit and a willingness to learn. Most of the folks we hired did not have prior StratOps experience. I also tapped into my network and the best people I had worked with in previous companies to build the core team.?

Next, we didn’t have enough people to interview since it was a new team. I am eternally grateful to leaders from our Customer Success and Analytics team for chipping in to help. For context, for our first 2 interns, I went through 2500 resumes and we interviewed 60+ people. No candidates were hired just because we needed to hire for a role.?It wasn't a hiring problem to solve, it was whether we would be able to get the outcomes we wanted from the people we hired.

Ramping up the team was again not easy. I was working hands-on on projects and also had to personally onboard each hire to the team. I wanted everyone in my team to handle projects end to end irrespective of designation or experience. Only the complexity of projects handled would vary based on experience/seniority. A lot of StratOps teams have a hierarchy of Analyst > Program Manager > Manager, where each one has a defined role. This leads to blockers and dependencies and slows down the speed of execution significantly, which I wanted to avoid. Further, new hires were given the freedom to choose their first project to ensure they feel confident and are able to deliver value immediately in their areas of interest.

There were days I was completely drained, swamped and close to burning out but the passion to build an impactful team kept me going. The immense support from my manager also contributed greatly to this. The focus was also on ensuring that with coaching, we build a culture focused on Postman values.?

Focussing on Outcomes

As a people manager, I realized very early on that the buck stops with me for all the team members and it was on me to help them get independent and perform in line with their talent and capabilities. I might not be executing all the projects, but the accountability was with me for all of them.

I had to balance deadlines and also give the freedom to the team to make mistakes and learn from them. Setting up the structure of the team, the operating cadence, and improving efficiency to the point of delivering results as well as avoiding burnout despite deadlines was challenging. Making the team think in different ways, and giving them the confidence to be comfortable sharing ideas and making mistakes have been immense learning for me but now, the team is able to run experiments without the fear of failure.?

As a GTM StratOps leader, it is important to think beyond the StratOps function and think about the overall business. Fundamentally, any SaaS business has 2 goals.

1. Acquire new customers and $$$
2. Retain existing customers and expand them

Any project that we take up has to lead to the above or improve the way we do the above.

The above intense focus on outcomes ensures 2 things?

• The team is very very lean (we are 25% to 30% the size of StratOps teams in other similar-sized organizations)
• We can easily prioritize projects based on urgency/importance and execute blazingly fast

This focus on outcomes and prioritization becomes extremely important when we support a 150+ employee GTM Org across multiple domains, and get a large number of requests from stakeholders all the time. The team is also extra motivated when they know and see the outcomes of their work.?

Internal Process

Documentation - Can't stress this enough. Anything we work on is documented, on Confluence/Google Docs depending on what it is about. And they are organised in an easily searchable and accessible way. Today, we are able to go back to past projects, understand them better with the documentation that we have and use them whenever applicable in current projects. The other advantage is - it reduces unnecessary calls. We are able to send status updates and past projects as Confluence links instead of getting on calls to explain to stakeholders. Most of our calls are only for decision-making.?

Transparency - Like most of the teams at Postman, we use JIRA for managing projects. The JIRA board is open for everyone at the company to track what we do and how we do it. We work on four-week Sprints which are planned in advance and send out status updates to GTM leadership every 2 weeks. This happens like clockwork.?

Iterative work - All our projects are iterative and we build on what we have. We incorporate feedback with every iteration. This helps keep us on track and we are usually not in a place where we have spent a lot of time doing something without outcomes. In the earlier days, I reviewed each deliverable before it was shipped. Now, we have faster iterations with peer reviews.?

Weekly Standups - We support 10+ teams and often, at this scale, knowledge gets siloed. To ensure this doesn't happen - Our weekly standups are internal demo days where you present your previous week's work to the team. An open feedback loop here also ensures continuous improvement and avoids replication of work. Everyone in the team is aware of what everyone else is working on.?

Feedback - Although I have frequent 1:1 with my teams for review and feedback cycles, we use them to discuss future career progression and goals. Project and work-related feedback are instantaneous. Feedback goes both ways and the feedback I have received from my team has helped me improve a lot as a manager.?

Tactical to Strategic shift - In the first year, we spent a lot of time firefighting. We had to plug gaps in the process, acquire data and verify its accuracy, ensure the CRM captured what we needed etc. As these tactical asks got resolved, we focussed on moving the team to execute Strategic projects with a broader focus.? We made a framework and slowly moved the team away to value-driven work. We learnt to say ‘No’ wherever appropriate and understand the scope of projects better to avoid rework.

Setting the culture

There are other cultural/behavioural aspects I try to reinforce with my team:

1. All decisions are taken with Postman's values in mind - https://www.postman.com/company/about-postman/. Important to be aligned with the overall vision of the company.

2. No tardiness - As a team, we value punctuality and appreciate when people join calls and meetings on time, and deliver work before deadlines (that we commit to). Yes, there will be times when scopes change, and personal issues come up, but those are very rare.

3. Being Proactive - We know we are here to solve hard problems and believe that the best ideas can come from anyone. Folks are encouraged to be independent and find gaps they want to solve. As a manager of self-starters, I do not tell my team what to do on a day-to-day basis.

5. Reading and Learning - Everyone is encouraged to read and discuss learnings. Having a book allowance helps. Everyone in the team recommends books they found useful and shares a summary. Listening to customer calls and joining/watching recordings of every all-hands and demo day is mandatory. Business folks need to know the product.

6. Taking responsibility - We have a bias for action and accountability. For any work that my team does, the buck stops with me. When we make mistakes, we own up to them. I encourage my team to fail but fail fast. And not to make the same mistake twice. The team is given the freedom to make mistakes and learn from them and ask for help whenever necessary without fear of judgment.

7. Pride and Happiness -

Before we deliver on something, we ask ourselves, “Am I proud to put my name on it?”

This is a philosophy that my time at Freshworks ingrained into me. We take our work seriously but not ourselves. Ensuring we are happy and having fun with our work and its impact is important. That's when you do the best work of your life.

The difficult part here is not setting the culture or saying it once, it’s reiterating it time and again to make sure they are adopted across the team and become the norm.?

What hasn’t changed - The Day 1 Feeling

I still wake up every morning, look at our growth dashboards, and think - Wow, this cannot be possible. I am able to drive outcomes and see them come to fruition in real-time. I work with amazing leaders and peers such as Sanjeev Sisodiya , Kyle Russell , Ryan Reynolds , Sam Jones , Prudhvi Vasa , and Harsha Chelle , who challenge me to do better and support me in every way possible. I know that I am doing the best work of my life so far.?

Despite all the work done and accomplishments over the last 2 years, there is a lot more to do and it still feels like Day 1.