Tailscale
Small (~290)
Together AI
Small (~150)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Together AI
Best for: Open-source AI infrastructure builders who want research-level impact at a startup
Ratings
TailscaleTogether AI
4.4
4.1
Overall
4.5
3.8
Work-Life Balance
4.5
4.3
Culture & Values
4.4
4.0
Comp & Benefits
4.2
4.0
Senior Mgmt
4.2
3.8
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 82% Recommend
👤 85% CEO Approval (Vipul Ved Prakash)
Culture Values
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Together AI only
🔓 Open Source🌱 Learning & Growth🤝 Flat Hierarchy🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven
Pros & Cons
Tailscale
- Same pay worldwide with 26 weeks parental leave and genuine work-life balance
- Brilliant, nerdy CEO who deeply understands the tech — culture is intellectual and respectful
- Career progression limited — only 3.0/5 on career opportunities
- Middle management still developing — some growing pains as the org scales
Together AI
- Open-source AI infrastructure — real mission alignment, not just marketing
- Small team with outsized research output; your work has direct impact
- Early-stage means wearing many hats constantly — not for specialists
- Limited career ladder; growth paths are still being defined
Bottom Line
Tailscale
Intellectual, engineer-led culture with same pay worldwide and 26 weeks parental leave — but career progression is limited and middle management is still maturing.
Together AI
Choose Together AI if you want real open-source mission with outsized research output — but expect to wear many hats.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Together AI — 49 jobs
💻 Engineering
19
🧠 ML / AI
9
📊 Data
4
📋 Product
3
🎧 Support
3
📣 Marketing
2
💼 Sales / GTM
2
🎨 Design
1
⚖️ Legal
1
⚙️ Operations
1
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Together AI scores 4.1/5.0 overall with a 3.8 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent. Together AI also emphasizes Open Source, Learning & Growth, Flat Hierarchy, Wears Many Hats.
On the hiring front, Tailscale has 52 open roles and Together AI has 49 open roles.