Overview
You're the first growth hire at a 3-person YC company building an AI ticketing system. You'll own the entire GTM motion: building outbound sequences to reach engineering leaders, setting up inbound funnels (website, content, demo flow), running early sales conversations, and figuring out what messaging actually converts. This isn't a specialized role—you're doing sales, marketing, ops, and everything in between.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Generalist (Growth + Sales hybrid) |
| Sales Motion | Building from scratch - initially outbound-heavy |
| Deal Complexity | Consultative (selling to eng/product teams) |
| Sales Cycle | Unknown - likely 2-6 weeks for early adopters |
| Deal Size | TBD - early pricing discovery phase |
| Quota (est.) | No formal quota yet - success = pipeline + revenue traction |
Company Context
Stage: Pre-seed / YC S25 (Summer 2025 batch)
Size: 3 employees (you'd be #4)
Growth: Just out of YC, onboarding "more teams every week" per post—likely 5-15 customers
Market Position: Category entrant - competing against Linear, Jira, Asana, Height, and other issue tracking tools. Positioned as "AI-native" vs legacy platforms.
GTM Reality
Pipeline Sources:
- 10% Inbound initially - YC network, word of mouth from early users, website traffic (minimal)
- 80% Outbound - you'll be building this from zero: cold email, LinkedIn, maybe cold calling
- 10% Community/Content - creating content to establish thought leadership in AI tooling space
SDR/AE Structure: No SDRs - you're doing everything. Founder might help close bigger deals but you own pipeline generation and most sales conversations.
SE Support: None. You demo the product yourself. Founders may join for technical deep-dives but don't count on it.
Competitive Landscape
Main Competitors: Linear, Jira, Asana, Height, Monday.com, plus newer AI plays like Dust, Puzzle
How They Differentiate: Auto-tracking via Slack/Email/GitHub integration - promises to reduce manual ticket creation. "AI-native" positioning vs legacy workflow tools.
Common Objections:
- "We already use Linear/Jira and it works"
- "How accurate is the auto-tracking?"
- "What happens when it creates wrong tickets?"
- "Seems early/unproven"
Win Themes: Speed to value (plug into Slack instantly), eliminates manual ticket entry grunt work, stays synced with dev velocity automatically.
What You'll Actually Do
Time Breakdown
Outbound (35%) | Sales Convos (25%) | Marketing/Content (20%) | Ops/Analysis (20%)
Key Activities
- Building outbound sequences: Researching eng leaders at Series A-C startups (likely ICP), writing cold emails, testing LinkedIn messages, tracking what gets responses. You're doing the manual scraping and sending initially.
- Running sales conversations: Taking demos, explaining how auto-tracking works, handling objections about accuracy and change management, negotiating pricing (which doesn't exist yet—you'll help define it).
- Creating inbound assets: Writing blog posts about ticket management pain points, recording demo videos, optimizing the website copy, maybe starting a newsletter. You're the content team.
- Setting up infrastructure: Building the CRM (probably HubSpot or Attio), creating email sequences in Instantly or Smartlead, setting up analytics, creating sales collateral from scratch.
The Honest Reality
What's Hard
- You're selling category change - prospects already have a ticketing system. You're asking them to rip it out and trust a 3-person startup's AI. Most will say "we're good."
- Pricing is undefined - you'll be figuring out what customers will actually pay while trying to close deals. Expect awkward pricing conversations.
- Wearing every hat is exhausting - one hour you're writing cold emails, next you're demoing, then you're debugging tracking pixels on the website. No specialization.
- Early product means broken demos - the product will have bugs. Prospects will ask for features that don't exist. You'll lose deals to product gaps.
- Founder dependency - critical decisions need founder input but they're building product. You'll wait on things or make gut calls that might be wrong.
What Success Looks Like
- Getting 5-10 demos booked per week from outbound within 3 months
- Closing 3-5 new customers per month by month 6
- Building a repeatable outbound motion that the next hire can scale
- Establishing Janet AI's positioning and messaging that resonates
Who You're Selling To
Primary Buyers:
- Engineering Managers / VPs of Eng at Series A-C startups (50-200 person companies)
- Product Managers who own workflow tooling decisions
- Occasionally CTOs at smaller companies
What They Care About:
- Reducing eng time spent on ticket admin - devs hate updating Jira, they want to just code
- Keeping tickets in sync with reality - chronic problem where ticket status doesn't match actual work
- Minimizing tool switching - they live in Slack/GitHub, want tickets to live there too
- Proof it works - need to see the AI is accurate, not creating noise
Requirements
- Experience building outbound motions from scratch (ideally at another early-stage startup)
- Have personally closed deals before - you need to sell, not just generate leads
- Comfortable with ambiguity and changing priorities daily
- Can write compelling copy (emails, website, sales decks) without a marketing team
- Technical enough to demo dev tooling and talk to engineers credibly
- Willing to be in SF office daily - this is in-person, founder wants high collaboration
- Self-starter who doesn't need structure - you'll build your own processes