Sales Operator (Enterprise)

DataDrone Inc.; Cheyenne, Northern (WY, KY); Hybrid; USD 90,000 - 150,000; Full time

Job summary

DataDrone Inc. is seeking an experienced B2B SaaS sales professional to close enterprise deals across multi-location brands. You will run discovery calls, deliver buyer-specific executive summaries, and hand signed deals to onboarding with complete context.

You will maintain CRM discipline, qualify before pitching, and focus on account growth and renewals starting day 45. This role emphasizes infrastructure-focused selling over generic tools.

Qualifications

• Proven B2B sales experience in SaaS, martech, operations tooling, or infrastructure.
• Ability to run discovery calls and surface buyer pain without pitching in the first 20 minutes.
• Proven ability to produce concise, buyer-specific executive summaries within 48 hours.

Responsibilities

• Run discovery calls using a structured 5-phase framework and qualify before pitching.
• Deliver executive summaries within 48 hours of qualified calls.
• Negotiate and close deals with multi-location brands (25+ outlets).
• Hand off signed deals to Onboarding with complete context to avoid surprises.
• Position account growth and renewal from Day 45, not contract expiry.
• Maintain the B2B Sales System and all sales templates.

Skills

B2B sales

SaaS sales

Discovery calls

Executive summaries

CRM discipline

Tools

Salesforce

CRM platform

Job description

DataDrone builds 0-1 SaaS products and the team that ships them. No bosses, no managers — the playbook manages, the copilot tracks. Every role owns a small, defined space with extreme accountability. We sell the SaaS product to multi-location businesses as infrastructure, not as a tool — and the difference matters in how we sell.

What You'll Do

You'll close enterprise deals for multi-location brands that already have outlets, already have customers, and are already frustrated that their current operation doesn't reflect what actually happens on the ground. You'll run discovery calls, deliver demos, produce proposals, negotiate terms, and hand signed deals to the onboarding team — with every detail they need to activate.

You sell infrastructure: the product installed across the customer's footprint, with outcomes that compound month over month. You never pitch a "tool." You pitch outcome.

Daily Rhythm (How You Operate)

• Per call: qualify against the Qualification Scorecard before pitching, then run discovery using the 5-phase framework — don't pitch in the first 20 minutes.
• Within 48 hours: deliver a buyer-specific executive summary — their words, not a template.
• Daily: keep every deal in CRM with a stage, next action, and close date.
• Per close: hand off to Onboarding with complete context — zero surprises.
• From Day 45: position account growth and renewal, not at contract expiry.

Key Responsibilities

• Run discovery calls using a structured 5-phase framework — not winging it
• Qualify every deal against the Qualification Scorecard before pitching
• Deliver executive summaries within 48 hours of qualified calls — specific to the buyer, not template
• Negotiate and close deals with multi-location brands (25+ outlets)
• Hand off signed deals to the Onboarding team with complete context — zero surprises
• Position account growth and renewal from Day 45, not contract expiry
• Maintain the B2B Sales System and all sales templates

What We're Looking For

• Proven B2B sales experience — SaaS, martech, operations tooling, or infrastructure. Closing, not just pipeline.
• You can run a discovery call that surfaces buyer pain without pitching for the first 20 minutes.
• You can produce a one-page executive summary that makes a VP want to bring their team into the next call.
• You maintain CRM discipline: every deal has a stage, next action, and close date. No exceptions.
• You can qualify out. Disqualifying a bad-fit deal cleanly is as important as closing a good one.
• You handle objections by reframing, not retreating.

Bonus Points For

• Experience selling to multi-location businesses — QSR, hospitality, fitness, retail, franchise, healthcare
• Experience with infrastructure or platform sales (not just SaaS subscriptions)
• Experience with a B2B CRM platform
• Comfort with AI copilots for research and proposal drafting

The Mindset We Hire For

• Infrastructure, not marketing. You sell what gets installed and what it produces — not a dashboard, not a tool, not a "solution."
• Qualify before you pitch. The scorecard exists for a reason. No proposal before qualification.
• Their words, not yours. The best proposals quote the buyer's own articulation of the problem.
• Speed signals seriousness. Executive summary within 48 hours. Follow-up within 24 hours.
• Clean disqualification is a skill. Disqualifying cleanly is as valuable as closing.
• Never promise what doesn't exist. The trust you build by being honest outlasts the deal you'd lose by overpromising.

Success in This Role

• 30 Days — B2B Sales System internalized. Product positioning understood. First discovery call run. CRM discipline established.
• 60 Days — Pipeline building. Proposals landing. Qualification scorecard applied consistently. Handoff quality validated.
• 90 Days — First deal closed. Pipeline consistently growing. Forecast accurate. Win/loss patterns identified.

Why Join Us

You won't cold-call from a script. You won't demo a product nobody wants. You won't chase unqualified leads to hit a vanity number.

You'll sell infrastructure to operations leaders who are already frustrated with the problem the product solves. The pipeline is built by the Outreach team. The product is proven. The discovery framework is structured. Your job is to convert qualified conversations into signed deals — and hand them off so clean that the onboarding team never has to ask "what did you promise them?"

5 hours of focused sales work per day. Quality over volume.

Self-Check Before You Apply

• Can you run a 30-minute discovery call where you don't mention the product for the first 15 minutes — and still have the buyer leaning in?
• When a prospect says "we already use a competitor," do you reframe — or retreat?
• Can you produce a one-page executive summary specific to a buyer within 48 hours?
• When you disqualify a deal, do you document why in CRM — or just stop calling?
• Is every deal in your current pipeline in CRM with a stage, next action, and close date?
• When you hand a deal to onboarding, could they activate the account without calling you?