For startups, a good Board is better than no Board, but a bad Board is worse than anything. One component of a good Board is a high value add Independent Board Member, which in my experience, often doesn’t get added early enough (for a variety of reasons). But sometimes the CEO takes the initiative to recruit an absolute gem and that was the case with ResQ, a software startup servicing the hospitality owners and service/repair vendors. It was serving on that Board where I first met Nilam Ganenthiran, back while he was an executive at Instacart. He brought relevant operating experience and a great perspective into the room, representing not the CEO, not the investors, but *the company,* which is exactly what you want from an Independent. We developed a friendship as part of our Board service and a recent blog post of his made me think I wanted to learn a bit more about his Instacart experience. So what follows are Five Question with Nilam.

Hunter Walk: You started at Instacart in 2013, just a year after it was founded, which obviously turned out to be an epic decision. Was it a case where you already knew folks there and had confidence in them, or some other aspect which gave you reason to join?

Nilam Ganenthiran: The story of me joining Instacart in 2013, is actually rooted in an epic bad decision. I was introduced to Apoorva, the founder of Instacart, in the spring of 2013 by my close friend/business school neighbor Rafael Corrales. Rafa runs Background Capital, and is one of the best partners for early company builders I know. Apoorva was ideating on his next project and was delving deep into the grocery sector. I was a consultant who had spent my career, starting at the age of 16 and working as a cashier in a grocery store, in and around the grocery industry. We started ideating on the concept of Instacart, which originally was going to be an e-commerce first grocery service with small micro-fulfillment centers in dense urban centers (think of the original concept as being similar to the quick-commerce industry which would emerge 5-6 years later). Apoorva was looking to bring on a non-technical co-founder as he entered YC, and my epic bad decision was not to jump at the opportunity to join Instacart at that moment. My wife and I were thinking about starting a family, we were happily living in Toronto, and I did not have the risk appetite to leave a secure job to join a startup. 

About 10 months later, I was about to go on extended paternity leave with the birth of our daughter Sita, and was at my going away party. I got a text from Apoorva asking if we could reconnect. I coincidentally had been doing a project for a large grocer focused on e-commerce and had more confidence that this was a service that needed to exist for consumers, and that grocers would not be able to solve this problem sufficiently themselves. I flew to San Francisco to meet with Apoorva, Brandon and Max – who were working out of a house in South Park – and after the first week of ‘helping out’ as an advisor around the office I fell in love with the team, energy, and infectious ‘just get it done’ spirit. I knew I wanted to help build it from the ground up. I called my wife from SFO before boarding a red-eye flight back home to Toronto and told her that we needed to talk when I got home, as I wanted to quit my job and join Instacart. We talked about it and it honestly was not a controversial decision. In the conversation I remember us circling on this idea –  “I don’t think this will work, but if it does, Sita (who was three weeks old) may never do her groceries in a real store”. 

In retrospect, it was not a very well thought out decision. We made it based on a gut feeling, a desire to be part of something that had a chance to make a big difference, and trusting the team building Instacart.

HW: The whole ‘get on rocketships without worrying about seats” – you ended up moving through Instacart in a variety of business and strategy roles before assuming the President role. Were “what’s best for Instacart” and “what’s best for Nilam” aligned the whole time, or did you encounter moments where you needed to raise your hands to advocate for yourself? What advice do you have for people in fast-growing companies about being a team-player but also taking advantage of the unique opportunity it provides?

NG: This is a hard one as I think I struggled with the conflict for a long time. This is likely cynical, but as companies get bigger the ratio of decisions based on “what is right for the company” vs. “what is right for the decision maker” skew towards the later. The good news is, this is not necessarily a bad thing since there is usually alignment between what is best for the decision maker and company. The best companies and cultures seem to have figured out this balance over time despite scale – but it is hard.  

I had the privilege of being an exec at Instacart for 8-years. There were year’s where I felt that I was sacrificing my own growth and career development for what was best for the company. There were other year’s where I felt the company was making bets on me to figure out problems which I had no experience to solve. Looking back, the encouraging thing is that over a multi-year period I never felt like I was getting the short end of the stick. It definitely required patience (and often self control), but the sheer volume of problems to be solved in startups allows for lots of opportunities to grow and take on stuff which is not in your direct domain. Over time, if you prove yourself as being able to consistently solve those problems, you will earn the right to take on more and more scope.

HW:  I loved a recent blog post of yours on “Code Yellows,” basically a call-to-arms sprint where a leader can focus as many resources as they need on solving an existential challenge. Did you ever encounter internal resistance – either from other leaders or ICs – to the Code Yellows and how did you handle? Seek to explain and enroll, or basically tell them if they don’t want to work on Saturday then they don’t need to work on Monday either?

NG: Thank you – I have gotten a lot of feedback on the post (both from people who agree with the premise and those that don’t) – and I am glad it struck a chord. 

We absolutely encountered significant resistance, typically internally and from functional leaders, to code yellows. The push back usually boiled down to some version of: “We have this great plan that we spent a number of weeks documenting, socializing, and cascading through the organization. You are now asking me to do away with this plan, MY plan, and go tell the team to do something else. I am going to look stupid. Or worse, you are going to think I am stupid because at the end of the year I would not have hit the goals we set out together at the beginning of the year.” Of course, another aspect of the push back which usually was left unsaid, was “this will burn out the team”. 

There are a few tactics that worked for me in seeking enrollment when we needed to pivot work in a sharp way and increase intensity – like during a Code Yellow:

• Explain why again and again: A big part of a leader’s job during a code yellow is explaining why a code-yellow is necessary, and what the consequences (to customers, users, the company, etc) would be in not focusing on this and getting it done. It can be draining but I have found that if people don’t buy into the need for a code yellow, results will be slower than if you had buy-in. We had code yellow’s fail, and a commonality with those was that the teams involved likely did not agree with leadership that it was actually that important. 
• Have clear exit criteria: Given you are asking the team to work outside of normal operating hours and push themselves to make meaningful progress, it is critical that you define and stick to a clear exit criteria. Code yellows cannot be a ‘hack’ to drive more productivity from the team. You will lose engagement (and eventually lose people) if they feel that goal posts of what you are seeking to achieve move. 
• Celebrate incremental progress: Code yellows are tough. They are all consuming. In the middle of this intensity teams can forget basic niceties and view positive feedback as being unnecessary. I have found the opposite to be true. Positive affirmation of progress on the journey out of a code yellow, and quickly acknowledging/celebrating small wins is critical to keeping motivation and boosting morale.

HW: You’ve had the chance to serve on a number of Boards – in fact that’s how we met, working on behalf of ResQ. What advice would you give a startup CEO about how to shape an effective Board and use them wisely? Are there consistent mistakes you seem first time CEOs making with their Boards?

NG: Board work, especially working with younger startups, has been one of the most rewarding things I have gotten to do in my career. Not only has it allowed me a way to share what I have had the benefit of learning during the journey building Instacart, but it has allowed me to keep learning myself – from new situations faced by these companies, and from my fellow board members. For example, I feel like I have learned so much from you Hunter, as I have watched you advise the ResQ team over the past 5+ years. 

Board construction is really challenging, especially in a startup. You may not always have a choice regarding who is designated to serve on your board from an investor. The energy and excitement with which your board engages with you may wax and wane with their views on how the company is performing, or worse still – based on how their own careers are progressing within their investment firms. 

There are two big mistakes, which hopefully I won’t fall into myself at Beacon, that I see CEOs making with regards to their Boards:

• Treating the board meeting as a chore: I have found that prepping for board meetings is a gift. It is a forcing function to get everyone internally on the same page on progress-to-date, it is a driver of accountability, and it forces thinking regarding go-forward plans. You should start thinking about your next board meeting just after finishing your previous board meeting (assuming you run quarterly meetings). I typically have a Google Doc going where I have some quick bullet points of an outline and key points I want to show at the next meeting. I find this helps me now during the quarter how things are going, and it makes the actual creation of board materials so much easier/less of a scramble. 
• Treating the board as a customer to sell: Yes – board members are important stakeholders, especially since they have the power to fire you (or not give you more money to fuel the business). However, I think viewing your board as an audience to be ‘sold’ to instead of a partner in your journey will orient your board to be less trusting and collaborative. People who serve on boards are usually smart. They know when they are getting a hyper polished version of the facts. Treating your board in this way will have them have their guard up looking for inconsistencies and the “gotcha’s”. I have found it is easier just to explain your thinking, being relatively transparent, and seeking engagement from your board members on problem solving – vs. pretending you have it all figured out.

HW: Explain Beacon Software to me and you think the time is right for an entity like this?

NG: Beacon Software is a new company that my co-founder Divya and I started earlier this year. We are a forever holding company for exceptional software businesses that serve niche or specific customer bases. We believe there are multiple ways to deliver great software to users. While building software companies from scratch is great, Beacon was formed to take advantage of this unique moment where the cost of development is rapidly falling, thanks to the proliferation of co-pilot tools and software engineering agents. We aim to acquire outstanding businesses run by owner-operator entrepreneurs and integrate them into our centralized technology, business process, and GTM stack to re-accelerate growth and margins. At its core, Beacon exists to expand the scale of the ambitions of the great entrepreneurs we partner with and to continue delighting the Main Street businesses for whom these companies have built software.

Thanks so much Nilam!