Overview
You're the first sales hire building the go-to-market motion for LMNTL, an AI accounting platform launching at a profitable company that already runs Minute7 (time tracking) and HourTimesheet (DCAA compliance). You'll cross-sell AI features to existing customers, cold-call government contractors for new logos, and create the playbook as you go. No SDRs, no sales managers, just you and the CEO.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Founding Full-cycle AE (self-sourcing + closing) |
| Sales Motion | Outbound-heavy with warm base for cross-sell |
| Deal Complexity | Consultative (explaining AI value + compliance needs) |
| Sales Cycle | 4-8 weeks (existing customers), 2-4 months (cold GovCon) |
| Deal Size | $10-40K ACV (estimate based on time tracking + AI premium) |
| Quota (est.) | $400-600K/year (likely ramping structure) |
Company Context
Stage: Bootstrapped, profitable (3 employees, self-sustaining)
Size: 3 employees (you'd be #4)
Growth: Launching third product (LMNTL AI) after establishing Minute7 and HourTimesheet
Market Position: Niche player in time tracking/compliance for professional services and government contractors. Not competing with Gusto/ADP directly, more specialized tooling.
GTM Reality
Pipeline Sources:
- 40% Cross-sell to existing Minute7/HourTimesheet customers (warm base, already trust the company)
- 50% Outbound to government contractors (cold calls, LinkedIn, researching DCAA-compliant firms)
- 10% Inbound from website/content (minimal - this is a small team with no marketing engine)
SDR/AE Structure: No SDRs. You do all your own prospecting, qualification, demos, and closing.
SE Support: No SE support. You'll need to learn the product deeply enough to demo technical features yourself.
Competitive Landscape
Main Competitors:
- For time tracking: TSheets (Intuit), Harvest, Toggl
- For GovCon compliance: Deltek, Unanet
- For AI accounting: Unclear - this is new category creation
How They Differentiate: QuickBooks integration, DCAA compliance focus, AI-driven accounting insights (new product)
Common Objections:
- "We already use [existing time tracking tool]"
- "How is this different from QuickBooks itself?"
- "We don't need AI in our accounting" (education required)
- "What if the AI makes mistakes with our books?"
Win Themes: Save time on manual reconciliation, catch billing errors automatically, DCAA compliance without hassle
What You'll Actually Do
Time Breakdown
Prospecting (40%) | Active Deals (35%) | Product Learning (15%) | Internal (10%)
Key Activities
- Cold outbound to GovCon firms: Research companies that need DCAA compliance, call finance/ops leaders, send LinkedIn messages. Expect low response rates - government contractors are hard to reach and slow to change systems.
- Cross-sell existing customers: Call current Minute7/HourTimesheet users, explain the AI accounting product, try to upsell. These conversations are warmer but you're still educating them on why they need AI for accounting.
- Run full demos yourself: Walk prospects through time tracking, DCAA compliance features, and AI accounting capabilities. You need to know the product cold - there's no SE to hand off to.
- Build the sales process: Document what's working, create email templates, figure out pricing objections, write case studies. The CEO expects you to create the playbook, not follow one.
The Honest Reality
What's Hard
- You're alone: No sales team, no manager to coach you, no SDR to fill your calendar. If you don't prospect, you don't eat.
- Category creation is slow: AI accounting is new. You'll spend a lot of calls explaining why someone needs this before you even get to product fit.
- GovCon sales are painful: Government contractors move slowly, have complex procurement, and are risk-averse about changing financial systems.
- Product is still evolving: You're launching a new product. Features will be missing, bugs will happen, pricing might change. You'll need to manage expectations and sell vision.
- Founder-led chaos: With 3 employees, priorities shift fast. You might get pulled into product feedback, customer success, or marketing tasks.
What Success Looks Like
- Close 1-2 deals per month in first 6 months (ramping)
- Convert 15-20% of existing customer base to AI product within year one
- Document repeatable outbound motion for hiring future AEs
- Identify 2-3 ideal customer profiles that convert fastest
Who You're Selling To
Primary Buyers:
- CFOs/Controllers at professional services firms (50-500 employees)
- Finance/Ops leaders at government contractors
- Accounting firm partners managing multiple clients
What They Care About:
- DCAA compliance without manual work (government contractors)
- Catching billing errors before they lose revenue (professional services)
- Real-time financial visibility (CFOs tired of waiting for month-end close)
- Not disrupting their QuickBooks workflow (integration anxiety)
Requirements
- 4+ years selling B2B SaaS (at least 2 years as full-cycle AE)
- Comfortable with no playbook - you've built sales motions before or are okay figuring it out
- Can handle rejection and low response rates on cold outbound
- Willing to learn technical product deeply (no SE support to rely on)
- Experience selling to finance/accounting buyers or government contractors is a big plus
- Self-motivated (no manager breathing down your neck, but also no one to push you)
- Comfortable with founder-led company chaos and wearing multiple hats