Four-day workweek
Client work and meetings run Monday to Thursday. Friday is kept clear so the rest of the week can be done well.
Do work you are proud of. Keep room for the rest of your life.
Second Mile has worked a four-day week for years. Monday to Thursday is for clients and for each other. Friday is the room that lets us do our best work the rest of the week.
“I've been so impressed by the amount of work we're able to accomplish within a focused four-day workweek setting. It's refreshing to work somewhere that prioritizes relationships, family, and personal growth.”
What a four-day week asks of us.
A shorter week does not mean less work. It means the work has to be chosen well, owned clearly, and handed off cleanly, so that the fifth day stays open more often than not.
Focused work has a boundary.
You will know what you own and why it matters this week. Meetings earn their place, priorities are written down, and Fridays stay clear of meetings unless something makes one necessary. Some weeks Friday is a day off. Some weeks it is the quiet day that gets the week finished well. Either way it is yours to use.
Curiosity is part of the job.
HubSpot changes every quarter and every client's business is different. We expect you to keep learning, to say "I don't know yet" and then find out, and to bring the question nobody else has asked into the room.
Relationships change the result.
Clients describe us as teammates, and that starts inside the company. We share context early, say the hard thing kindly, and assume good intent, across disciplines and time zones.
Benefits that make the work sustainable.
The four-day week is the one people ask about first. It is not the only one.
Paid time away
Time to rest, travel, and care for people, on top of the three-day weekends.
Health and wellness
Medical, dental, and vision coverage, with an HSA option.
Financial benefits
A 401(k) with employer matching, life insurance, and role-based incentives.
Family leave
Paid leave for new parents, including adoption.
Distributed work
Remote by default, with the flexibility and the accountability that go with it.
Sabbatical
A paid sabbatical after seven years with the company.
Open roles.
Every role here works directly with clients and directly with the founders. If nothing below fits and you think you belong here anyway, the last paragraph is for you.
Full-time · Remote · US
Account Strategist
Apply for this roleRun client engagements from discovery through handover: the person a client calls, the person who decides what gets built next, and the person who makes sure the team can run it afterward.
Full-time · Remote · US
Solutions Architect
Apply for this roleTurn a client's business into a HubSpot architecture: the data model, the integrations, the scope, and the proposal, then stay close enough to the build to make sure it holds.
Contract · Remote · Anywhere
HubSpot, web, and data contractors
Apply as a contractorWe are always looking for experienced contractors to work alongside the team on HubSpot builds, web development, and data and integration work. Contract work is open to people outside the US. Send us what you have built and how you like to work.
Second Mile is an equal opportunity employer. Hiring decisions are based on merit, performance, and business need. If the work fits and you do not meet every listed qualification, apply anyway; we would rather hear from you.
Common questions
How does the four-day week work in practice?
Client work and meetings run Monday to Thursday. Friday is kept clear of meetings unless something makes one necessary, and what you do with it depends on the week: some Fridays are a day off, some are the quiet day that gets the week finished well. A quarterly team meeting or a conference sometimes lands on one. The point is that four focused days do the work of five, and the fifth day gives you room.
Do I need to live in a particular place?
Full-time roles are US-based, and the team works across Nashville, Portland, and Charleston with most days remote. Contract roles are open to people outside the US.
What does the hiring process look like?
An initial interview, then a project that reflects the real work, then an interview with the leadership team. We meet final candidates in person, either you come to us or we come to you. You will know where you stand after each step.
Do I need HubSpot experience?
For most full-time roles, yes, and it is one of the first things we look for. Developers and data architects do not necessarily need it, because the work they do sits beside HubSpot rather than inside it.
Meet the people you would work with.
The team, the values, and why the company was started.
About Second Mile