I wrote a blog post last month about my job search as an ex-Founder. In the blog, I talk about how I used my network to help me figure out what I wanted to do next with my career. I was originally unclear on the kind of role I wanted, but through many different conversations and experiences, I was able to conclude that I wanted to take on a Chief of Staff or People Ops type of role. These were roles that I felt would leverage my strong people skills and allow me to focus on my passion for company & culture building.
It probably comes as no surprise that publishing this first article was also a way for me to broadcast that I was looking for CoS/People Ops roles, and market why I would be good at them. 😄
A month later, I’m excited to be publishing “Part 2” and to announce that I’ve started a new journey with Dover as Chief of Staff. 🎉
I interviewed with just under 30 companies as a result of my posts, and I learned some interesting things along the way. I used these learnings to create a framework for evaluating jobs.
In this article, I’ll be breaking down that framework, and how I ended up choosing Dover.
✨ A Quick Note On Applying for Jobs Online ✨
Before I dive in, I want to share one of my biggest takeaways from this entire experience:
Applying for jobs online is the worst way to get hired.
In my search for a dream role, I wrote blogs, reached out to friends, asked for intros, posted on forums, and applied to jobs online. Between July 15th (the week I posted on Medium/Bookface) & August 5th (the day I accepted an offer), I entered just under 30 interview processes. 100% of these interviews happened as a result of my blogs, my Bookface post, or through introductions. Jobs I applied to online, in most cases, are only just now getting back to me, if at all.
The market data about hiring supports my findings.
So, to all the jobseekers out there: be aware that most of the job market is hidden. What you see posted online is just the tip of the iceberg. Hiring managers should be aware of this dynamic, as well, and understand that many of the best candidates are not applying to posted roles, and are looking passively instead.
🏆 Project Management 🏆
I mentioned above that I entered a little under 30 interview processes between July 15th & August 5th (about three weeks).
I used Airtable to track all of my conversations and rank my interest. Juggling interview processes is like having a full-time job in and of itself. Especially as you enter later stages, and companies want you to start working on small projects, or doing on-sites*.
Airtable helped me manage things in the beginning, but pretty quickly, I needed to start prioritizing the opportunities I was most excited about, or they would start slipping through the cracks.
So how was I able to distinguish the 5-star, gold, premium, extra guacamole type opportunities from the rest? I came up with a quick evaluation framework.
*on-sites were virtual, of course, because of COVID-19.
🔍 An Evaluation Framework 🔍
By interviewing as much as I did, I eventually started noticing some patterns or indicators that a company was a fit for me, or not.
The positive attributes & standout elements I was looking for were People, Product, Potential, Path & Pay. Or… the 5 Ps.
There were also some negative behaviors I picked up on in other interview processes that made me think twice, or turned me off to the company. Blow-up offers, backpedaling, blocking, boys clubs, babysitters, and bets. Or… the 6 Bs.
(This is super extra & annoying of me, so I really do hope someone finds this helpful 🤓)
This quick framework helped me to spot my top companies faster, and helped me focus on what mattered. This framework also helped me to de-prioritize those companies where I thought I might be wasting time.
If you’re evaluating companies or offers right now, check out this framework and see if it brings you any clarity.
If you’re a hiring manager, see if you do any of the things on the Bs list, or if you can find a way to make the 5 Ps shine more in your candidate process.
The Dover team did an incredible job of recruiting me (no surprise, as Dover’s tagline is the modern recruiting agency) and I will be bringing in examples to highlight that.
✅ The 5 Ps
I want to work with people I like, respect, and could see myself becoming great friends with. People I can learn from, and who will have a positive influence on me. People who are empathetic and care about me, personally. Leadership who wants to empower me to be my best and help me develop my skills.
There were many strong, initial signs that Dover was full of great people:
- Whenever I mentioned in conversations that I was interviewing at Dover, the people from my network would tell me how highly they thought of Max, George & Anvisha (the founders). They did this without me even asking. Everyone seemed to know them & love them.
- I felt seen throughout the interview process. Example: Max (Dover’s CEO) personally reached out to me after reading my post, and explained why he thought I would be a strong fit for Chief of Staff at Dover. This is actually something Dover does for its customers — and clearly, it works. Later on, George (COO) remarked to me that he saw my top skill as communication, and listed several concrete examples where he’d already seen that. It made me feel great to know that he recognized this in me, and to know that my skills were being acknowledged.
- After Max sent me the offer, several team members sent me notes to congratulate me and express their excitement for me to potentially join. These small gestures leave a very strong impression.
- Max kept me in the loop throughout our interview process and never dropped the ball. He also got my cell number early on, and would text me occasionally with updates rather than emailing me. This kept Dover at the top of my mind and not lost in my inbox.
- Finally, when I was given the offer there was no rush or pressure for me to accept. Although I did accept within a few days, of course. 🙂
I want to work on something I feel personally connected to. I want to work on a product that I believe in and am proud of. Something I know is good. When I care personally about the problem I’m solving, and I know the product is good, my job becomes easier. It’s easier to sell, to recruit, to market, and to pitch investors — because my heart is in it, and I really believe every word I’m saying.
There were many strong, initial signs that Dover would be a great product for me to work on:
- I knew some of the customers listed on Dover’s website — so I reached out, and asked them to tell me what they thought. These references only had positive things to say about the solution and the customer experience they’d had.
- I have a lot of natural empathy for Dover’s customers, and the problems they are trying to solve. Not too long ago, I was a founder, and recruiting was one of my challenges. I know what it’s like, and I can see the value that Dover provides, immediately.
- When I was working on Cherry, something my co-founder and I would often geek out on was the idea of completely modernizing the HR suite. This included benefits (like Cherry), comp, feedback loops, training & development, and of course — hiring. Dover fits squarely into that and felt like a natural continuation of the work I had already been doing. A continuation of the mission that has been driving me for the last few years.
I want to work on a rocket ship, meaning: I want to hit a home run. I want to experience hyper growth at a company, and see from the inside how things evolve and scale. I want to understand what it takes to build a successful company and build on what I was able to do at Cherry. Because of that, I wanted to choose a company with a lot of momentum.
There were many strong, initial signs that Dover has great potential:
- Recruiting is a $50B industry in the US — so I know the company is tackling a huge market.
- Dover has identified a compelling problem: Outbound recruiting is a numbers game, but keeping the quality high is hard. Many companies turn to recruiting agencies to solve these problems, but all of the largest recruiting agencies still operate by using manual processes, spending hours on administrative work.
- Dover has created a compelling solution: they’ve built advanced ML-powered matching software to find the perfect candidates for a particular role. Their NLP outreach system reaches out to those candidates in a highly personalized way. Dover is automating the entire recruiting stack, from sourcing to scheduling. This is a huge opportunity 🙂
I want my next role to help me “level up” as a person and as a contributor in every way. I want to learn as much as I can, and to set myself up for success. I want to build upon my skills and become a more and more valuable person to my company, and to my industry as a whole.
There were many strong, initial signs that my path at Dover could take me anywhere:
- After publishing my initial article, I was oscillating between being a Chief of Staff or People Ops. I felt attracted to both roles because I felt that both would allow me to use my strong people skills, and focus on my passion for company building. However, I got a ton of feedback as I interviewed that I should pursue CoS roles, and not limit myself to People Ops. After all, I’m only at the beginning of my career, and I have so much time to specialize in People Ops if I wanted to a little ways down the road.
- Chief of Staff is a unique role with a broad scope of responsibilities. I will not be limiting myself to any one department.
- As CoS, I’ll get continued exposure and chances to work on financing & fundraising. These are key parts of the business most other roles don’t get to see.
- As CoS, I’ll also “get my masters” in this market. These kinds of roles need to know their stuff & stay on top of market research so they can help create roadmaps, GTM strategies, and work on product.
- I’ve been mentioning how much I want to use my EQ in my professional life, and as a CoS I won’t be limited in where exactly those skills go. I’ll get to leverage my interpersonal skills in Sales, Marketing, Customer Success and Partnerships.
- And of course — I’ll have the opportunity to learn about & work on “People”. Interviews, onboarding, team cohesion, retros, feedback loops, and broader HR responsibilities.
- Overall: I won’t be limiting myself to any one domain too early in my career. Instead, I’ll get to continue to improve myself across multiple areas and develop expertise in what I feel drawn to. This role is a business driver, and that makes me feel extremely motivated. I know that if I succeed, the possibilities for my career are endless.
Not much needs to be said about this one. I had a number in mind that I was looking for & knew I wanted a role that valued me in line with the market. Of course I wasn’t going to accept or reject an offer based on salary & equity alone — but it was an important part of my decision making process.
Overall, Dover hit the mark on each of these categories and I felt extremely confident accepting the offer. I think that if a company can emphasize these five elements to their candidates, they have a better chance of closing them.
Now — let’s talk about the 6 Bs, or the 6 behaviors that actually turned me off, personally, and helped me de-prioritize certain opportunities in order to focus on better ones.
❌ The 6 Bs
❌ Blow-up Offers
Otherwise known as “exploding offers”. This is when a company extends an offer to a candidate, but only gives them 24–48 hours to accept, or lose the job.
Choosing a job is a big, long term decision for me and the company. I think these kinds of offers would start my relationship with my employer off on the wrong foot. I want to be excited and comfortable accepting an offer because I genuinely want it, and not because I was pressured into it.
It’s never a good feeling when a founder or hiring manager gushes that they are ready to hire me — only to start back pedaling and adding more steps to my interview process the next time we speak. Backpedaling can take a variety of forms, but always leaves me feeling skeptical & second guessing the company.
When founders or hiring managers make a habit of overpromising and underdelivering during interviews, I fear that these patterns will continue even after I join, on other important issues: promotions, relocation, strategic decisions, expense approvals, and other new hires.
Many people experience “blocking” during their career. Blocking is when someone is up for a job & everyone on the team is excited about their joining, but someone on the decision making side isn’t comfortable, because they actually want the role, themselves. In some cases they can actually prevent the new person from joining.
To me it’s a red flag when it appears as though someone in the org tries to block things from happening in an effort to protect their own career path. At a startup, the company should be more important than any one individual and their career goals. Because the company is bigger than you, me or anyone. I want to be on the same page with others about this — I don’t want to work in environments where egos will interfere with the company reaching its full potential.
❌ Boys Clubs
I was in final rounds of another company’s interview process when I realized that I would actually be the first female hire on a team of 14 men. This made me uncomfortable and I realized I probably wouldn’t enjoy working there. I made it a point to look out for diversity in my interviews going forward.
I think Dover is an excellent example of a diverse team. They have 3 founders, 1 of whom is female. Including myself, the team is 4 women and 7 men. This makes me feel confident, knowing that Dover values the contributions of all people. Some startups use the excuse that they are too small to be worrying about diversity, but Dover is an example of a small team that has managed to be diverse. It can certainly be done.
I say “boys clubs” to keep with my “B” theme but of course diversity goes much deeper than just gender diversity. I would also feel very uncomfortable working on a team with little or no racial/ethnic diversity, or working for a team where everyone went to the same school, etc. At the end of the day, diverse teams are smarter, more creative, and just do better work. If a company has poor diversity, I have to wonder why.
Misalignment of values is obviously going to be a huge reason that one would not accept a job. For me, that misalignment becomes clear when I notice “babysitting” behavior.
I’ve been enthusiastically working multiple jobs since I was in high school, and I’m a former founder — I *love* to work! Work enriches me and makes me happy. I am motivated to be successful in everything I do.
But I notice that when I work in environments where leadership is distrustful, babysit their direct reports, or make others feel lazy and self indulgent for the time they take away from work… something weird happens. I start to lose my natural drive and motivation. I resent being watched like a hawk and I notice that these kinds of managers will inadvertently kill morale for other team members, too.
❌ Bets & Gambles
On this point, I’m referring to when a company takes a bet or a gamble on you, calling the hire “opportunistic”. This is not so much of a red flag for me — just a yellow one!
I find that the best possible circumstance is one wherein the company feels a strong need for a particular kind of hire. They are missing something and have strong opinions and ideas about how an additional team member will fill in the gaps. They’ve done the work ahead of time to figure out what success looks like for this hire, and how the role will scale.
When a company is hiring opportunistically, I imagine it’s possible that they haven’t thought the role through all the way. If the company doesn’t have strong idea about my role — I fear I will end up in an awkward position when it’s Day 1 and neither the founders nor I know what I should be spending time on. Or, when it’s Day 100 and suddenly there isn’t a need for my role anymore. If the founders & I haven’t decided what success looks like — then I’m set up for failure.
Be aware of this as you search, and if you are looking at an opportunistic role, just make sure to have these conversations ahead of time and things will work out.
📖 Beginning a New Chapter 📖
I’ve really enjoyed this process of learning & sharing what I’ve learned.
If you can think of some — please leave a comment telling me *your* “Ps and Bs”, or other memorable moments from your interview processes. I would love to hear. 🙂
By Gillian O'Brien