Chief of Staff to CEO

About Rootly

At Rootly, we are a mission to be the go-to way companies respond when things go wrong, helping every organization be more reliable. We do this by building an industry leading incident management platform that allows companies around the world consistently and quickly resolve incidents. We are not simply transforming an industry, we are carving an entirely new +$B segment ourselves and need incredible talent to achieve this ambitious goal together.

Customers love Rootly. Some of the fastest growing companies around the world such as NVIDIA, Figma, Canva, Tripadvisor, Squarespace, LinkedIn, Wealthsimple, and more rely on Rootly to power their critical incident management process. They obsess over our delightful enterprise-ready platform and unique partnership model. See why our customers have reviewed us 5 stars on G2.

Investors love Rootly. We are backed by some of the most respected funds in the world from Y Combinator to operators like the CTO of Dropbox and GitHub. We'd be happy to disclose our entire funding and profitability picture live during the interview. As a culture we relentlessly put transparency first. We conduct monthly financial reviews as a team so everyone has a pulse on the health of the business and publish what we are building in our weekly changelog.

About the Role

Written by JJ, co-founder and CEO of Rootly.

I am so excited to open up our first Chief of Staff role here. Why? I need to spend more time on our business than in our business. That is where my time and leverage are best used. This role is a true all-access front row pass to how a fast-growing startup is constructed. There is no detail or decision you won't be aware of or a part of. You can single-handedly look back and say you've forever changed our trajectory for the better.

You should expect the CoS role to change and evolve over time. In fact, it may change week-by-week. But you'll really be my most important thought partner and execution engine. What this role isn't is an admin assistant. I have an amazing EA already that does that.

Here are a few areas you might be working on.

• Strategic Gaps - as we continue building out the foundations of the company, there isn't necessarily a need for a "full-time" person in every function. Sometimes in various parts of operations, product, HR, finance, there are jobs to be done and need a jack of all trades that can fill in that gap / figure out the permanent solution.

• Product / GTM - think of this as the glue of the organization. Helping take major products to market and the strategy around it. Solving problems like how we ensure all the marketing pieces are lined up with how CS will communicate to existing customers / any gotchas along the way, competitive analysis, etc. Solid product knowledge and instinct will make you effective and dangerous here.

• People - I keep the bar for quality, pace, and execution extremely high. Your job is to help continue setting that standard and find ways to measure it. Everything from ensuring we don't have wasted/duplicate efforts, effective meetings, codifying our values, employee engagement, all hands, ensuring we are focused on the same goal/rowing in the same direction, figuring out where we have critical bus factors, talent management/levelling, etc.

• Special projects - I index heavily on running experiments. Someone that can help me run those 0-1. Everything from finding out our best billboard/OOH strategy to a strategic brand partnership with a customer to founder marketing on a particular topic. This requires a ton of outside the box thinking as 99% of the time no one has done it before.

• Finance / Ops - help with investor/VC relationships, external accountants, tracking our spend/burn, vendor management/cost reduction, creating company-wide policies, HR related issues, financial forecasting/budgeting. Preparing for board meetings. A strong finance background and analytical mindset is important.

About JJ (CEO)

Written by JJ, co-founder and CEO of Rootly.

Working with me is not everyone's cup of tea, and my team will transparently give you the unfiltered version. I am relentless in my pursuit of helping Rootly win and am incredibly resourceful. I rarely play by the rules (in fact, I enjoy breaking them and challenging the status quo) and love helping us carve our own path. I rarely copy-paste playbooks or blindly take advice from elsewhere, hoping it will work here.

You'll love working with me if you have a great sense of humor (I really do try to be the funniest on the team, but we have stiff competition), are detail-oriented (I obsess over being in the details), impatient, and enjoy experimenting. I have deep empathy and care for our team and customers. I welcome being challenged, am often the first to admit I am wrong, but the thing that rubs me the wrong way is not trying. Not succeeding is okay, but not trying is not.

If you want to get a sense of my style, listen to this podcast with Brian Chesky (CEO @ Airbnb) from 25:00-30:00. It describes how I like to operate and how I want our leaders to operate quite well. If you ask anyone on the team, there is no job I am unwilling to do or is above me. Whether that is writing Figma copy for a new shiny product at 2am or teaching our new sales hires how to cold-call, I will always step up to the plate. I don't expect that to change regardless of our scale. I don't think you'll like working with me if you aren't comfortable multi-threading, juggling one too many things at once, don't want to be pinged after 5pm, blunt feedback, and sometimes acting on instinct rather than data.

For my background, well, that's all on LinkedIn. I don't think I am particularly special or gifted but I am deeply passionate about what we are building, serving our customers, and helping give our team the best careers possible. That seems to work so far!

The Ideal Candidate

• At least 3 years of management consulting (MBB), investment banking, VC/corp dev, or start-up operational experience, bonus if you've been in SaaS before.

• Located in Toronto, this will require being in-person (not everyday necessarily but can't be a 2hr+ commute away).

• Pride in being the jack-of-all trades. You are excited to be exposed to and have a say in multiple company functions.

• Strategy is 30%, and execution is the other 70% that gets you to the finish line. Your uncanny advantage is your strong strategic thinking coupled with your speed for execution. For teams you work with, you are known for bringing operational velocity - which is speed with a clear direction.

• You have a low ego and are willing to learn. You are willing to admit to mistakes and have an open mindset to new avenues of problem-solving.

• You take extreme ownership. There are no tasks or problems that are beneath you - even the most unsexy or complex.

• You are able to drive critical goals under ambiguity and constraints.

• You know how to solve (not oversolve/invest) in the problems at our scale. Most often perfection is not required. Always speed and execution is required.

Benefits

• Comprehensive medical, dental, and vision

• 3 weeks vacation + unlimited sick/mental health days + company-wide shutdown EOY

• M3 MacBook Pro of choice

• $1,000 for health and wellness

• $1,000 for home office

• $1,000 for visiting a teammate located in a different geography

• Learning and advancement budget at your discretion

• Ground floor opportunity to be an early member of a fast growing venture-backed startup

Rootly is an equal opportunity employer. We aim to create an environment where every team member at Rootly feels like they belong so they can have a greater impact on our business and customers. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.