Role: Enterprise Sales Director
Role: Enterprise Sales Director
Phase: Post-pilot — hired when 3–5 paying customers exist and the product is stable Engagement type: Full-time employee Budget: $85,000–$95,000 base salary; OTE $130,000–$160,000 When to hire: After 3 paying customers validate the charter model and the founder can no longer personally manage a full sales pipeline Status: Do not hire until charter pilot revenue is real and repeating
Why This Role Exists and When It Becomes Critical
The founder sells the first 5–10 customers. This is non-negotiable. The founder knows the product, knows the customer’s world, and has the credibility to say “I built this because I ran a crew.”
After that, the sales motion is validated and documented. At that point the founder needs to be:
- Building the product and platform
- Managing integrations with Aspire, QuickBooks, ADP
- Running the Field Ops Coordinator
- Raising the next round if needed
Not managing a 40-account pipeline. That is what this person does.
This hire must be able to sell without the founder on every call. If they require the founder to close every deal, they are not ready.
What This Person Sells
Primary product: Actual — a hardware + cloud field truth platform for landscape management companies. Pricing at $149–$249/crew/month at the time of hire (may scale with badge count per deployment; see pricing doc).
The decision maker: The landscape company owner, or the VP Operations at a company large enough to have that title. Not the field supervisor. Not the IT director.
The value proposition this role must be able to deliver in < 90 seconds: “Your payroll is based on timesheets your crew foremen fill out at 5pm on Friday. Actual gives you GPS-verified, badge-confirmed job site presence — so you know which crews were on which properties, for how long, whether they arrived on time, and whether the job was completed before the crew left. No manual entry. It syncs with Aspire and feeds directly to your payroll system.”
If the candidate cannot say that from memory on day two, they are not the right hire.
Responsibilities
Pipeline Generation
- Build and manage a qualified pipeline of 50+ landscape management companies across the Southeast US (initial territory), expanding nationally after Q2
- Cold outreach by phone and email — this role does its own prospecting at this stage; no SDR to hand off leads
- Attend one landscape industry trade show per quarter (NALP Landscapes, state-level lawn and landscape associations, Aspire user conferences)
- Work the Aspire user community and LinkedIn landscape business owner groups
Sales Execution
- Conduct discovery calls to qualify budget, decision-making authority, crew count, current timekeeping method, and pain level
- Deliver product demonstrations using real data from a pilot customer account (with permission)
- Manage deal cycle from first contact through signed agreement
- Produce and negotiate quotes, service agreements, and pilot terms
- Hand off signed customers to Field Ops Coordinator for deployment
Revenue Target
| Period | Target |
|---|---|
| Year 1 (first 12 months in seat) | 20 new paying crews signed |
| Year 2 | 50 new paying crews signed; begin managing renewals and expansions |
One “paying crew” = one customer company deploying one or more crews on a monthly subscription. A company deploying 5 crews counts as 5 against quota.
Market Intelligence
- Report monthly on: objections heard in the field, competitor activity, pricing resistance, feature requests from prospects (not customers — the Field Ops Coordinator owns that)
- Flag if a major competitor (ClockShark, Busybusy, Aspire’s built-in time module) is actively targeting the same accounts
Candidate Profile: Required
Non-negotiable:
- 5+ years in B2B field service software sales, or sales specifically into the landscaping / lawn care / property services industry
- Must have sold software that field crews use, or sold to landscape company owners
- Must speak operator language naturally: crews, properties, invoice cycles, equipment routes, seasonal capacity, H-2B visas, plant hardiness zones, bid season
Why this is non-negotiable: A candidate who has only sold enterprise SaaS to IT directors or procurement departments will fail. The landscape company owner will stop the call within 90 seconds if the salesperson doesn’t understand that “we pull up to the site” means the crew is driving a truck and trailer and the first 10 minutes are equipment unload time.
Track record required:
- Quota attainment at >80% for at least 2 of the last 3 years
- Has sold deals averaging $15,000–$60,000 annual contract value
- Can provide 2 customer references from landscape or field service accounts
Candidate Profile: Strongly Preferred
- Has sold Aspire, ServiceTitan, Jobber, or similar field service management software to owner-operated or PE-backed companies with 10–100 field employees
- Has experience selling hardware + software bundles (not just SaaS)
- Knows the regional landscape market: NALP member companies, state associations, PLANET-certified firms
- Familiarity with Power BI or dashboard-based value demonstration
Candidate Profile: Automatic Disqualifiers
- Only enterprise SaaS experience with 12–18 month sales cycles and procurement departments
- Has never spoken to a field operations decision maker
- Cannot explain the difference between a landscape management company and a lawn care company
- Requires a large SDR team to generate leads
- Previous employer was a CRM or HR software company selling to an office-based buyer
Compensation Structure
| Component | Amount |
|---|---|
| Base salary | $85,000–$95,000 |
| Commission | 10–15% of first-year contract value, paid on signed agreement |
| OTE (on-target earnings) | $130,000–$160,000 at quota |
| Benefits | Standard package |
| Equity | 0.25–0.5% (4-year vest, 1-year cliff) |
| Accelerators | Commission rate increases to 20% for deals closed above quarterly quota |
Commission is paid on signing, not on collection. The company takes the collection risk. If a customer cancels within 90 days, there is a clawback on 50% of the commission.
Interview Process
Step 1 — Phone screen (30 min): Ask: “Tell me about the last landscape management company you sold to. What was their crew count? What problem were you solving? Who signed the deal?” If they can’t answer specifically, end the call.
Step 2 — Domain knowledge interview (60 min): Ask them to explain the landscape company owner’s payroll problem without any prompting. Ask about Aspire — have they touched it? Do they know what property-level job scheduling means in that context?
Step 3 — Live discovery call roleplay (30 min): Founder plays the landscape company owner. Candidate conducts a cold discovery call. Evaluate: Do they get to the real problem? Do they listen? Do they try to demo too early?
Step 4 — References: Call at least one landscape or field service customer reference. Ask: “Did this person understand your business before they tried to sell you?”
Known Risks
Risk: Hire with great field service experience but whose territory was exclusively West Coast or Midwest; limited Southeast landscape market knowledge. Mitigation: Accept this. The founder’s Southeast market knowledge covers initial territory. Hire the best operator vocabulary candidate, not the closest geography.
Risk: Excellent seller who over-promises during demos and creates customer expectations the product cannot meet. Mitigation: Demo scripts must be approved by the founder. No capability may be demonstrated that is not live in production today.