When students finish their studies and earn their college degrees, their outlook tends to be hopeful and filled with opportunities; their choices are seemingly endless. When John graduated in 2009, he walked into a job market that was anything but that. The first few years of his career began with a merry-go-round of dead-end minimum wage jobs and a road ahead that would be filled with twists and turns that nobody could predict.
In 2013, following a few years of bouncing around, he found the path of entrepreneurship - opening his own design consulting business. Over the next few years, John would learn how to run and grow a company by the art of action - quickly learning how to put one fire out after another. This accumulation of knowledge allowed him to create his second business - a news media company that covered the tech, innovation, and entrepreneurship community titled StartNow Pittsburgh. While running both simultaneously, his continued efforts sparked a deep passion for building businesses and scaling startups which taught him the value of community.
During the spring of 2021, following the sale of StartNow Pittsburgh, John began to look for ways to take his operations knowledge to the next level and discovered the On Deck Chief of Staff program. Without hesitating, John applied to be a part of the 2nd cohort.
Aligning the stars between the future (On Deck) & his next challenge (Four Growers).
Although his discovery of the On Deck Chief of staff program came first, his next opportunity wasn’t far behind. Only about a month after applying to the program, John landed his next opportunity and was hired as a Chief of Staff for an AgTech robotics company called Four Growers based in his hometown. The stars had aligned, and within 30 days, John kicked off his next career move and joined an On Deck program that would take his skills to new heights.
Before he knew it, John was drinking from a fire hose in his new role with Four Growers. The company was founded on a mission to provide healthy, affordable, local produce by reducing the costs of greenhouse growers through robotics. John was excited; this wasn’t just a startup that was tied to the attention economy. It was a startup trying to solve a real problem in the real world.
Its first product, a tomato harvesting system for greenhouses, was getting ready to move from R&D into a commercialization phase. As employee #6, he was in charge of non-product-related departments (operations, HR, finance, marketing, and special projects). John had to become a swiss army knife—whatever fire popped up on a given day, it was his job to put it out.
On top of that, John was still trying to navigate the ebbs and flows of being a Chief of Staff - a role he had only been aware of for a year prior to beginning his time with Four Growers. The programming provided by the ODCoS cohort helped remove the mystery of the role as both speakers, and fellow cohort members shared their experiences and as John navigated the onboarding process. It helped him understand the constant context-switching that the Chief of Staff role requires, how to batch tasks, and how to build repeatable processes that can scale with the company.
With a new job secured and with the support of a community of like-minded peers, the excitement surrounding John’s career was something to behold. The community that On Deck offered was unlike any other group he had been a part of. The diversity in participants, industries, and skill sets was noticeable, and the cross-collaboration between everyone showcased a considerable value add from day one.
“After struggling to meet new people during the pandemic, the On Deck community was a breath of fresh air to my business network and my career. The program opened my eyes to the value of putting myself in the middle of new experiences and taking chances with professionals looking to achieve similar things. It wasn’t long before I started to reach out and have one-on-one virtual coffee chats with fellow ODCoS2 participants. Out of the 80 participating fellows, I purposely sought out conversations with at least 30+.”
As the Chief of Staff for a seed-funded startup, there are endless challenges to solve and processes to improve. From minor responsibilities such as day-to-day facility operations to developing a recruiting strategy to double the team, context switching is a required skill set. The ODCoS family was there for help whenever a new challenge arose.
“One of my main targets within the more extensive set of responsibilities was to lead and help navigate our efforts to double our staff (going from six to twelve) within the first six months of starting at the company. In addition, I had to review & solidify HR processes around an expanding team - which included employee reviews, handbook modifications, and strategies to recruit engineering talent. If I dealt with a situation I had little or no experience in, I knew I could lean on the ODCoS slack community to gain insight into how others approached these same issues.
Need help with what you’re facing at work? Post it for the community to review.
Regardless of the question, you’re bound to get eight to ten solid answers in 48 hours from the community. It was extremely beneficial.”
But the helpfulness of the community didn’t stop at Q&A. Often, the Chief of Staff role can be lonely - balancing being seen as a leader by employees while being trusted with a large amount of sensitive information.
“Being in this role is unique. And while it does come with many positives, I’ve often felt that I’m sitting on my own island from time to time. There isn’t anyone to turn to within your company for answers - leadership expects you to figure it out while the employees look to you for answers. Drawing and connecting with other professionals outside your company was invaluable.”
For example, John was tasked to develop a new standard for employee reviews, especially one that would scale with the company. Employee feedback is helpful for any organization but critical for a startup. Through the OnDeck community, John was able to review templates and standards from other members. They provided how they approached similar tasks and what metrics they relied on. The end deliverable was on John to create, but the data and insights he was able to gather through On Deck made the challenge easier.
The Art of Transferring Value
With any of the On Deck programs, the cohorts are filled with a wide range of diversity and are tailored for all professionals. However, the one thing that every participant is committed to is the pursuit of lifelong learning. John noticed that every fellow Chief of Staff cohort member always sought ways to improve their work performance while accelerating their careers. If you come to the program with a strong work ethic and desire to learn, you’ll thrive in the program environment.
“On Deck is a big melting pot of different ways to do things, approaches, and strategies. Everyone comes from diverse backgrounds, companies, and industries. You must be open to adopting distinct ways people do things and see if it applies to your situation. It could lead to you being 5%, 10%, or even 20% better at what you do. There’s a lot of knowledge and expertise that you can benefit from if you come to it with an open mind.”
While John found numerous opportunities to learn from the program, he also felt a need to give back. The generosity within the community encourages reciprocity amongst its members. And to be an outstanding participant, you need to give back in addition to receiving.
“It’s not about take, take, take. It’s about: How can I contribute to the group? What information can I share? What templates can I share? Or even being there for someone when they’re having a bad day. Is there a way that I can listen or provide guidance? I’m a big believer in investing in the group. If someone wants to invest in the On Deck program, I think the best way to get a lot out of the program is to give, give, give.”
John’s commitment to that led him down the path of sharing his experiences and knowledge with others. His previous roles as a COO allowed him to lead a presentation around the potential transition from CoS to COO, a change that many CoS want to make but find challenging to navigate. John discussed how to approach the leap to COO, what is often required, and how to determine if it is the right move for you. He looked at the frameworks to best position yourself for the role, what you’ll encounter along the way, and how the transition naturally ties into what you are already doing as a CoS. He also co-led another presentation around demystifying finances for non-financial Chief of Staffs, which covered how-to dive into reading financial statements, forecasting, understanding revenue, and figuring out costs.
Preparing for those presentations and answering people’s questions forced him to refine his understanding of the material - which often led to a win-win situation for John and those listening in. But it didn’t stop there. During the program, John often found himself in smaller conversations helping fellow members navigate tricky leadership situations and even helping one member strategize around asking for a $20,000 raise.
The On Deck Chief of Staff program was helpful to John’s skillset and had an immediate positive ROI. John found more than $7,000 in consulting work through the On Deck network, more than offsetting the membership cost John paid for out of pocket.
Although John’s program came to a natural end in the summer of 2022, the lessons learned & the friendships earned throughout his 12-month journey will last a lifetime. Yes, being a part of a valuable community takes time & commitment from the participants, but John wouldn’t have it any other way.
“The On Deck Chief of Staff program has been a constant blessing over the last year. Within the first few months, you have to build it into your life as if you took on a 2nd job, but the asynchronous nature of it all makes it easy. I would highly recommend anyone considering joining to speak with past participants and get a sense of the possibilities.”
Check out the On Deck Chief of Staff Fellowship.