Role description
ChargeOverExecutive Assistant — ChargeOver
Minneapolis (hybrid) · Full-time
Who we are
ChargeOver builds billing and subscription management software for B2B SaaS companies. We're a small, founder-led team — under 20 people — based in Minneapolis. We work for our customers, not for vanity metrics. We move fast, talk straight, and run the company on the parts of EOS that work for us.
We're co-founded by Ryan (CEO) and Keith (CTO). Everyone in the company knows who everyone else is and what they're working on.
The opportunity
We're hiring an Executive Assistant who is one part 1:1 executive partner to Ryan and one part operations engine for the company. The right person makes Ryan's time go to growth and team-building — and keeps the operational layer of the business humming without anyone needing to think about it.
The calendar and inbox work matters, but so does owning commissions processing, planning company offsites, building out the SOPs that keep recurring work on rails, and being a quiet, trusted coordination point across our team.
The challenge we're solving
Our outgoing EA built real ground here — vendor relationships, recurring rhythms, a working calendar. The role didn't break because she wasn't good at it. It broke because the structure around it wasn't built for what the work had become.
Two things specifically that we're fixing in this hire:
Hours match scope.
This is full-time. Our last EA was part-time at 29 hours a week, with a workload that regularly exceeded that. The new role is sized to what the work actually is.
Authority is explicit from day one.
We're not asking the next person to earn permission to act over six months. You'll have calendar autonomy, discretionary spend authority, and the ability to send email as Ryan from the start. The trade-off is that you'll be expected to build the scorecard and process documentation that holds you accountable to that authority.
This is a structural rebuild of the role, not a like-for-like replacement.
Success outcomes
What "great" looks like, with rough timeframes:
By day 30 — Commissions are airtight.
The end-to-end commissions process is documented as a checklist, signed off by Ryan, and run cleanly each cycle. Calendar is fully managed against Ryan's guidelines without prompting. You've established yourself as a trusted point of contact for the rest of the team.
By day 60 — The role has a scorecard.
Every metric is green. Calendar coordination runs without Ryan checking. You're surfacing proactive recommendations on how EA-owned processes should work across the company.
By day 90 — You're confidently making calls in Ryan's name on day-to-day work.
Calendar, inbox, and routine asks go through you without check-ins on each one. The bigger stuff — personnel matters, compensation, anything legally or strategically sensitive — still routes through Ryan. The "is this worth Ryan's time" filter lives in your head, not on a list of rules. You ask only when genuinely uncertain, and that list shrinks each month.
By 6 months — Recurring processes run themselves.
Every recurring deliverable has a living checklist, every checklist gets executed, and when something fails, you fix the root cause and update the system. Ryan's calendar reflects his actual priorities. He spends his time on growth and team-building, not coordination.
What you'll work with
The leadership team.
Ryan as your direct principal, plus working relationships with Keith, Tyler (Head of Growth), Chris (Director of Customer Success), and Bryan (Sales).
The tools we live in.
Google Calendar, Slack, Email, Notion, Asana. We meet you where the work already is — no new tools for the sake of tools.
Real budget authority.
Up to $250 discretionary spend on offsites, vendors, gifts, and the like. Above that, you'll bring options to Ryan and we'll decide together.
Hybrid Minneapolis.
Some days in office, some remote. Local to Minneapolis is required.
Why this is different
You're not slotting into a defined seat.
You're rebuilding the role with us. The structure, the scorecard, the documented processes — those don't exist yet. You'll help shape them.
The authority is real.
Decline meetings. Reschedule things to protect focus. Send email as Ryan. Spend money. You won't be in a "wait to be told" posture.
Half EA, half ops.
Roughly 50% of the week is direct support for Ryan — calendar, inbox, meeting prep, the work most people picture when they hear "Executive Assistant." The other 50% is company-level operations — commissions, offsite planning, vendor coordination, and the recurring processes that keep ChargeOver running. If you only want one side of that, this isn't the role.
You'll be the person making the company run smoothly.
That work is mostly invisible when it's working. We see it. We value it.
What we're honest about
There's a gap.
Our current EA leaves at the end of May. The realistic start date for the next person is late July or August. You'll inherit some things that have been in flux while we transitioned.
A lot of the operational knowledge lives in one person's head.
We're capturing what we can before she leaves, but you'll be building the playbook as you go. If "build the system while running it" energizes you, this is a great fit. If it sounds like chaos, it isn't the right role.
The pace is real.
Most weeks are manageable. Some weeks — offsite prep, quarter-end, an unexpected fire — will demand more. We don't want this to be the norm, and we'll build the systems to keep it from being so.
Our culture
We work async by default — Slack and email handle most of it. We measure things we care about and share the numbers. We say what we mean. We give people clear ownership and get out of their way. We try not to take ourselves too seriously, but we take the work seriously.
What we admire in the people who do well here: consistent, quiet excellence. No fanfare. Things done right, every time. Ownership when something goes sideways. The kind of person where six months in, Ryan says, "I wake up knowing they've got my back."
What happens next
- Complete application form.
- 30-minute intro call.
- 60-minute deep dive interview
- A paid practical exercise drawn from real recent situations — we'll pay for your time.
- References and a final round.
- Decision and offer.
We move fast. If you're right for this, you'll know quickly. So will we.