Incredible Challenge, Incredible Opportunity
Pros
I'll tackle this from a couple of angles. I joined this company with a few goals in mind after hearing about it through Y Combinator connections. I wanted to be a part of a team tackling a problem in the physical world, operating in an unglamorous space, and alongside people I felt like I could trust and go to battle with. I also knew that I had at least one big bet left in me - I have been a part of a few big 0 to 1 pushes in large corporates and at more stable startups, but have become, I suppose, enough of a risk-addict to where I wanted to raise the stakes further. All of these things have converged at PermitFlow to afford me and my coworkers an incredible opportunity to re-shape how we build and deliver physical spaces across the US. PermitFlow has delivered on every one of these dimensions and I've gotten everything I wanted out of the experience so far. Every trope or euphemism about startups you may have heard is true here 1. Priorities constantly change and evolve 2. Extreme ownership of both success and growth opps is required. 3. There are ample opportunities, once you've got your footing, to work across disciplines and across multiple different types of customer engagements. 4. The company has found strong demand in the marketplace for our service and software tooling. I have an incredible support system across the organization as well. I've met great friends, incredible talented folks from across many walks and disciplines, and have been forced to stretch outside of my comfort zone. I've also been publicly and privately credited for my work when it is impactful, am rewarded for my contributions, and feel valued as a person and an employee by nearly everyone I work with across every level of the organization. Management genuinely cares about people and wants to create a team full of top-performers, and retain high-quality talent. Generally transparent about the state of affairs at the company and what expectations are if you want to be successful at an abstract level.
Cons
Growth hurts - I've definitely had my fair share of moments where I want to give up and I've had to ask for help, spontaneously call a coworker to blow off steam, or just take a step back before re-engaging with tough problems. This is a Series A startup after all - there is a lot of ambiguity, the constantly shifting priorities can be painful or disappointing, and it hasn't all been a kumbaya experience. Things that matter to employees and employee experience - e.g., defining what career growth looks like for your role or area - are still works in progress to some degree. While this is understandable - keeping the business alive can cause tunnel vision at times - I think that when I first joined, I was unsure of what good looked like for me in my role, what growth looked like at the company, and how the company set and measured itself against goals as well. We're still figuring out performance management, but we've made a lot of strides and are dedicating smart, trustworthy people to the effort today. We are also still pretty early in our company journey - we're very analytical, sometimes to our detriment. There is pretty healthy tension between product, sales, and customer engagement, and sometimes I do wish we could move faster in automating aspects of our work, but I think our tech team is improving tremendously in terms of how they position and hold themselves accountable to pledges they make. I also think that, like many early stage startups, there's more opportunity than resources, and figuring out how to stack-rank and prioritize work, whether in tech, sales, CS, or otherwise, is a skill we're continuously improving. The work is hard, a lot is still being figured out, and we're working through those growing pains proactively and constructively, but that doesn't diminish the pain in the moment. Permitting and construction are fairly esoteric for people with traditional tech backgrounds, and vice versa for people with traditional construction management backgrounds. We're working to bridge this gap more effectively, but it's an ongoing experiment. This is part of why the opportunity here is so large, but it's not always easy to execute against.
