Hi — Liz here. 👋🏾

One of my favorite parts of reading dozens of job postings every week is seeing the perks companies offer to stand out. Up until this week, I’d been mildly entertained.

Then I saw a company offering a stipend of over $1,000 a month toward rent.

Other notable perks included breakfast, lunch, dinner, and the joy of working around 60 hours a week. Which makes sense, because apparently going home is just a concept.

Needless to say, they didn't make the cut. But the perk was worth noting.

And who knows? Maybe a cost-of-living stipend will become a standard line item in compensation packages someday.

Here’s to dreaming big.

Let's get into it.

🔎 How We Curate

Every role featured in Modern Admin meets the following criteria:

🧑🏽‍💻 Flexibility Matters — we prioritize flexibility, but great work can happen in person too
💰 Pay Transparency — if a company knows its budget, so should you
🤝 Culture Check — we look beyond the job description at the employee experience
🗂 Role Integrity — titles should match scope (no inflated or misleading roles)
🌱 Room to Grow — we look for meaningful ownership and career-building experience
🗓️ Still Hiring — every role is verified before we publish

$121.4K–$184.8K · Remote (US) · Full-Time
Industry: Technology / Cloud Software
Posted: October 23, 2026

Why we love it: Dropbox treats executive support as a partnership built on judgment. Working closely with the CBO and his Chief of Staff, you’ll help turn priorities into a well-run executive office. Its Virtual First approach also makes room for asynchronous communication and protected focus time.

The fine print: Bring 8+ years supporting senior executives, experience partnering with a Chief of Staff, and confidence using AI tools. Primarily Eastern Time hours, with occasional international scheduling flexibility and travel for team gatherings. Hiring is limited to US Zones 2 and 3; NYC, San Francisco, and Seattle metro areas are excluded. Salary varies by zone; bonus and equity are also offered.

$122.3K–$165K · Remote (US) · Full-Time
Industry: Footwear / Apparel
Posted: October 22, 2026

Why we love it: Great creative work needs good operations behind it. At HOKA, that means leading the Creative Project Management team, improving campaign workflows, and making sure resources match the workload. The emphasis on creative empathy, developing talent, and timelines grounded in reality caught our attention.

The fine print: Best suited to someone with 7+ years in creative operations, project management, or marketing operations within a consumer brand, plus 3+ years managing people and a relevant bachelor’s degree. Experience with global brands and creative teams is essential; expect domestic travel. Open to residents of AZ, CA, CO, IN, MA, MN, NY, OR, PA, TX, UT, and WA. The listed salary range is benchmarked to Goleta, CA; pay varies by location.

$80K–$100K · Remote (US & Ontario, Canada) · Full-Time
Industry: Insurtech / AI Technology
Posted: October 20, 2026

Why we love it: For someone ready to deepen their HR expertise, this role offers ownership of policies, employee questions, and the processes that support a growing team. There’s room to progress toward managing day-to-day HR operations, plus remote flexibility, equity, and a 401(k) with employer matching.

The fine print: You’ll need 2+ years of hands-on HR generalist experience, in-house multi-state compliance experience, and a bachelor’s degree. This small, high-intensity team puts payroll, benefits, and compliance directly in your hands—including an annual compliance audit and handbook refresh within your first 90 days. Hiring is limited to AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, and Ontario.

$135K–$200K · Remote (US) · Full-Time
Industry: Healthtech / Healthcare Navigation
Posted: October 22, 2026

Why we love it: Helping older adults navigate healthcare and stay independent gives this work a tangible purpose. As the first senior operations hire, you’ll partner directly with the founders to improve guide onboarding, plan capacity, and launch services. Healthcare experience isn’t required, opening the door to operators bringing expertise from other industries.

The fine print: The team is looking for 3+ years in operations, strategy, Chief of Staff, or a related role, with examples of processes you’ve improved or projects you’ve taken through implementation. Expect shifting priorities and hands-on work across frontline workflows, capacity planning, and service launches. Comfort with operational data is important. Equity is also offered.

$40–$65/hour · Remote (US) · Part-Time Contract
Industry: Technology / Outdoor Recreation
Posted: October 22, 2026

Why we love it: Looking for a part-time engagement that draws on your executive support experience? AllTrails needs 15–20 hours a week supporting its CEO and two additional executives. The scope includes calendars, travel, board coordination, and a leadership offsite—all behind a product built to get people outside.

The fine print: Candidates should have 5+ years of Executive Assistant experience, ideally supporting VP or C-suite leaders. The commitment is 15–20 hours per week for a fixed term described as 4–6 months. Contractors must meet device security requirements, including installing Vanta Agent; additional compliance requirements apply in certain states.

Your question:

“We’re a small company (~25 people). Our recurring meetings keep multiplying, and I’m not sure they’re all useful anymore. But I don’t know how to approach it with the founder without overstepping…”

Our take:

Facts are your friend. If you’ve talked to employees/managers and you have actual feedback, that is #1 in helping your case.

But even if you don’t, before you craft your pitch, do a meeting audit. Understand how many meetings each team is having (this is us assuming you’ll have enough access to calendars), and from there…put a price tag on it.

For example: If your software engineers are all included in a meeting with go-to-market every week, take their salaries and put an hourly rate on their time. Suddenly, five engineers who each make $200K spending an hour a week on a call that could be an end-of-week email or an async chat start to look very expensive. And time in meetings is time away from other work.

Money talks, and in your case, it supports the cause. 💰

INTRODUCING CULTURE AUDIT

The Culture Audit is a hands-on look at how your workplace operates day to day—what leadership intends, what employees experience and what needs to change between the two.

Assess. Design. Align. Implement. Activate.

→ Book a free Discovery Call