Founder-Led Content Strategist & Storyteller
Hi! I'm Debbie, CEO of Pineway.io - an AI-powered platform helping coaches replace 6+ tools with one system so they can stop drowning in admin and actually coach.
I'm looking for someone who can help me build a founder-led brand that people actually care about.
Think: Ali Abdaal, Lara Acosta, Meagan Nunez, Jun Yuh. Founders who show up as humans, not logos. Founders with content that feels like advice from a smart friend who gets it.
If you've helped tech founders, coaches, or creators build that kind of presence and can prove it drove real outcomes (signups, waitlist adds, DMs, engagement), I can't wait to meet you!
WHAT YOU'LL OWN
Content Strategy & Execution
- Own the content calendar for Instagram, TikTok, and LinkedIn
- Turn my voice notes, ideas, and frameworks into scripts and captions that sound like me
- Write hooks that stop the scroll AND make people think "this is for me"
- Ensure consistent, high-quality content ships every week
- Bring fresh ideas proactively; don't wait to be asked
Founder-Led Storytelling
- Help me show up as a real human building a real company
- Balance vulnerability with credibility (no toxic positivity, no guru vibes)
- Tell stories that connect emotionally but drive action
- Position Pineway as THE platform for coaches who refuse to burn out
Conversion-Focused Content
- Every post has a job: drive profile visits, waitlist signups, or customer conversations
- Track what's working and double down
- Work with our content intern on engagement and community building
WHAT SUCCESS LOOKS LIKE
Month 1: Content calendar running, 4-5 posts/week going live, clear brand voice established
Month 3: Content directly driving waitlist signups, DMs asking about product, coaches saying "I feel seen"
Month 6: Pineway known as a founder-led brand in the coaching tools space, content machine running smoothly
YOU'RE A GREAT FIT IF
- You've managed social for tech founders, SaaS companies, or creator brands
- You can write in someone else's voice naturally (not just templates)
- You understand founder-led content (it's different from agency/corporate social)
- You have examples of content that drove real outcomes (signups, engagement, revenue)
- You can show me work where the founder's personality came through
- You're self-directed: you bring ideas, you don't wait for briefs
- Your English is excellent (warm, direct, compelling, plus no fluff)
YOU'RE NOT A FIT IF
- Your portfolio is full of aesthetic grids, but no proof of impact
- You've only worked with restaurants, fashion, or lifestyle brands
- You think "founder-led content" means posting selfies with inspirational quotes
- You need detailed briefs for every single post
- You can't show me what your work actually made someone do
WHAT YOU'LL GET
- $1,500-2,000 USD/month (based on experience + portfolio strength)
- Raises tied to growth milestones (waitlist signups, revenue)
- Fully remote
- Work directly with me (CEO) & a small team. No layers, just fast decisions
- Early equity when you transition to full-time
- Front-row seat to building a brand from zero to something real
HOW TO APPLY
If you've read this far, here's what I would love to see:
- Record a 3-minute Loom video covering:
- Who you are and what you've worked on
- One specific example where your content helped a founder/brand grow (show me the work + the results)
- What excites you about working with an early-stage tech founder
- How you'd approach building Pineway's founder-led brand
2. Write 3 hooks for this Reel topic: "Why coaches are losing clients because of their tools" (Visit pineway.io first to understand what we do)
3. Share your portfolio link with examples of founder-led content you've created (Screenshots, links, anything that shows your work)
If you're the right person, I can't wait to meet you!
Talk soon!!
Debbie