Welcome!
Hey there, Flexperts!
If you've been doom scrolling career advice lately, you've probably noticed: millennials are having a moment. And by moment, I mean a full-blown "is this it?" crisis about work that promised flexibility but delivered burnout with a side of layoff anxiety.
The good news? There's a way out that doesn't involve rage-quitting or starting a sourdough business.
It's called a portfolio career. And it's how you stop putting all your eggs in one very unstable employment basket. I broke down why this might be the move in 2026 (and how it's different from the gig economy mess) over on Medium: Don't Get a Side Hustle in 2026—Get a Portfolio Career.
Now let’s get into today’s roles.
-Nesha
HR TECH
Contractor, UX Writer/Content Design // Pebl
Why it's worth a look: You'll architect the tone of voice for a global hiring platform operating in 185+ countries. High-stakes content strategy where your words literally need to work across cultures. You’ll shape how companies talk to their distributed teams.
What to know:
Contract, 10-20 hours/week
Flexible hours
You're auditing and building their product TOV framework from scratch, then stress-testing it in real flows
Collaborating with brand/marketing teams to extend (not duplicate) their voice into product
Potentially A/B testing to prove your strategic choices work
Good fit if:
You've built content guidelines and TOV frameworks before (not just followed someone else's)
The idea of stress-testing content across user flows sounds like detective work
ED TECH
Contract Career Coach // Stepful
Why it's worth a look: You'll coach graduates from underserved communities into Medical Assistant and Pharmacy Tech roles at places like CVS and NY-Presbyterian. Stepful just raised $31.5M and was named #1 EdTech company by TIME—so you're helping people access healthcare careers while the company's momentum is real.
What to know:
25-40 hours/week
$18-22/hour
Remote with 24-hour response expectations
Mix of group coaching and 1:1 sessions—resume reviews, mock interviews, job search strategy
You're coaching soft skills (empathy, teamwork, stress management) as much as tactical job prep
Tracking student progress and doing proactive outreach to keep them motivated
Good fit if:
You've done career coaching or counseling before (healthcare industry experience is a bonus, not required)
You're comfortable juggling group sessions and individual coaching without everything feeling rushed
The idea of helping people from underserved communities break into stable healthcare jobs feels meaningful, not just transactional
ED TECH
Contract Student Financial Success Coach // Stepful
Same company. You're the first line of support keeping students from dropping out when motivation tanks or payments get messy. Less about landing jobs, more about making sure they graduate first.
What to know:
Contract (1099), Monday-Friday availability (8 AM – 8 PM EST window)
$18-20/hour
You're coaching students through motivation slumps, grade struggles, and payment issues
Handling phone, email, SMS, and social media inquiries (current + potential students)
Using Front/HubSpot to track and resolve issues
Creating FAQs and documentation to help students self-serve
MENTAL HEALTH
Part Time Journey Guide (Educator) // Hero Journey Club
Why it's worth a look: You'll facilitate mental health and SEL classes inside Minecraft for kids and teens, making therapy 6x cheaper and 3x more effective than traditional approaches.
What to know:
Contract, part-time
2-10 PM EST window (most groups 5-10 PM EST)
Leading 50-min weekly sessions for groups of 8-10 inside Minecraft
Must have Master's in Teaching/Education + teaching license (or license-eligible)
Need 6+ months recent virtual classroom experience with 5th-12th graders
Experience with neurodivergent and LGBTQIA+ communities required
Must currently play Minecraft
AI
Contract Senior Technical Recruiter // Attentive
Why it's worth a look: You'll recruit engineering and product talent for an AI marketing platform that powers $10B+ in revenue for 8,000+ customers. Attentive's been on Deloitte's Fast 500 four years running and Forbes' Cloud 100 for five, so you're sourcing for a company engineers actually want to work for.
What to know:
6+ months
$50-62/hour
Full-cycle recruiting for Engineering and Product teams
FINTECH
Contract Frontline Support Specialist // Heard
Why it's worth a look: You'll be first-line support for therapists during tax season at a company that handles their bookkeeping, taxes, and payroll so they can focus on clients.
What to know:
Feb 1 - Apr 30, 2026
$24-27/hour, 40 hours/week
Available 8 AM - 8 PM ET window, Monday-Friday
Phone support is your primary channel (also email, chat, social media)
You're learning enough bookkeeping/tax/payroll to answer questions or route smartly
Using ticketing platforms like Zendesk or similar
NONPROFIT
Digital Content Freelancer // MissionWired
Why it's worth a look: You'll write fundraising emails, ads, and social copy for nonprofits like Sandy Hook Promise and Human Rights Watch—plus progressive political campaigns. MissionWired has converted $4.5B in donations, so your words are directly tied to mission-changing revenue.
What to know:
$25-40/hour depending on experience
Writing email, web, ad, and social copy across direct response campaigns (donations, engagement, list growth)
Ghostwriting in the voice of nonprofit leaders and Democratic candidates
Collaborating with client teams on strategy, messaging, and feedback loops
Participating in meetings as needed
WOMEN’S HEALTH
Freelance Community Moderator // Flo
Why it's worth a look: You'll moderate Secret Chats for the world's #1 women's health app (80M+ monthly users, $1B valuation). Flo reached 7M paid subscribers by earning trust at scale and now they need moderators to keep their community safe and engaging.
What to know:
1099; Any time zone
Monthly payments (rate not disclosed)
Moderating user-generated content: posts, comments, images in Secret Chats
You'll encounter sensitive content regularly
ED TECH
PT Contract Career Coach // Springboard
Why it's worth a look: You'll coach bootcamp grads transitioning into data science, UI/UX, machine learning, and coding roles—helping them land jobs at companies willing to hire career-changers. Springboard has a near-perfect placement rate and hundreds of job offers yearly, so your coaching directly impacts whether someone breaks into tech.
What to know:
12-25 hours/week (coaching calls only, admin billed separately)
$24/hour first year
Flexible hours (including weekends if you want), but students are full-time workers with families—so your availability impacts booking rates
1:1 and group coaching on job search for technical roles
Tracking outcomes in their CRM with detailed notes on risk factors and student progress
HEALTHCARE
PT Contract Recruiter // AdMed
Why it's worth a look: You'll recruit medical writers and business development roles for a pharmaceutical marketing agency during a focused hiring sprint. Short-term, high-impact work (3-4 months) with potential extension
What to know:
~30 hours/week (~4 days/week)
3-4 months with extension potential
Recruiting: Medical Writers, Account Executive, Assistant Medical Writer, Business Development Coordinator, Project Coordinator
FINTECH
Contract Recruiter (Maternity Leave Coverage) // Tradeify
Why it's worth a look: You'll do full-cycle recruiting for a fast-growing prop trading firm during a 6-month maternity cover—with strong potential to convert permanent. Tradeify operates at the intersection of performance, data, and community
What to know:
6 months (maternity cover), strong conversion potential
$65-75K annualized
High-volume hiring across trading, product, marketing, and operations
End-to-end ownership: sourcing, screens, hiring manager partnerships
EXECUTIVE MEMBERSHIP
Contract Programming Manager // The Suite
Why it's worth a look: You'll design and execute high-impact events (forums, off-sites, workshops, salons) for C-suite execs at companies like OpenAI, Anthropic, Airbnb, Uber, and a16z. The Suite has 5,000+ active members across their curated communities
What to know:
$8-9.2K/month with conversion potential to full-time
End-to-end ownership: agenda design, speaker outreach, networking experiences, run-of-show plans
Managing sponsor content and expectations
Using Airtable, AI tools (ChatGPT Enterprise), and automation to streamline workflows
High autonomy, fast-paced—you're expected to leverage historical docs and templates without hand-holding
💰 My FAVORITE Way to Earn Extra 💲
As a mom of four (under age 12), family vacations can be pricey. Add the rising costs of traveling and groceries and it’s easy to see why it feels impossible to do annually.
In 2022, I decided to create an income stream to make traveling groceries easier. That’s when I learned about market research.
I applied for opportunities while in car pool lines or getting stuck in traffic. And as someone who loves sharing my thoughts on products, experiences, or brands, market research was a no-brainer.
🙌 User Interviews helped me earn more than $3K! I was able to pay for a trip to Disney and reduce my monthly grocery budget.
Quick Reminder
I created Flexpert Jobs to curate professional, non-technical flexible work opportunities for busy people like you. These roles are always:
Remote First
Fractional, contract, or part-time work
Human vetted
Shared daily
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Until next time,
Nesha V. Frazier