HEAD OF SALES

ABOUT AR WORKFLOW

AR Workflow is a fast-growing SaaS company transforming how restoration companies and franchise operators manage accounts receivable and collections. With 1,800+ active users and clients like SERVPRO, Flood Rescue, and Restoration 1, AR Workflow helps multi-location businesses accelerate cash flow, reduce 60/90/120+ day AR aging, automate collections workflows, and give leadership real-time visibility into receivables performance.

The product was built by founders with 14 years in the restoration industry and 10 years running an accounting firm that served restoration contractors exclusively. This is deep product-market fit — 80% of growth to date has come through referrals. AR Workflow is now entering an aggressive outbound growth phase focused on scaling revenue operations.

We are not looking for someone to manage an existing machine. We are looking for someone to help build it.

THE OPPORTUNITY

This is AR Workflow's first ever Head of Sales hire. You are coming in at the ground floor of the sales function with full autonomy to build it your way. The founders are domain experts — not sales experts. They want a partner who owns this function completely and has the experience to execute without hand-holding.

The upside is real. Uncapped commission structure, milestone bonuses, and a direct path to VP of Sales as the company expands into new verticals. If you perform, this role grows with you.

ROLE DETAILS

• Location: 100% Remote — Latin America (any country) 

• Hours: 6:00 AM – 3:00 PM Pacific Time (9AM–5PM Eastern) — required for SDR team overlap 

• Employment Type: Independent Contractor 

• Reports To: Sam & Lori Frenzley (Founders) 

• Team: 2 SDRs + 1 AE (current) — scaling to 5–6 SDRs and additional AEs

CORE RESPONSIBILITIES

The Head of Sales is responsible for building and scaling AR Workflow's outbound revenue operation from the ground up. This is a highly hands-on leadership role. You are expected to actively participate in outbound execution, sales process optimization, pipeline management, and revenue accountability on a daily basis.

• Build and manage outbound prospecting systems from scratch

• Recruit, onboard, train, and manage SDR team (scaling from 2 to 5–6 reps)

• Manage distributed remote SDR team across multiple countries and time zones

• Source and organize qualified target accounts and maintain outbound lead lists

• Manage pipeline structure and CRM accuracy in HubSpot

• Assign and distribute leads across SDRs and Account Executives

• Establish outbound activity standards and KPI accountability

• Increase demo volume, trial activations, and paid account conversions

• Improve outbound messaging, positioning, and cold calling execution

• Implement structured forecasting, reporting, and weekly revenue accountability

• Build scalable outbound systems capable of supporting long-term growth

90-DAY PERFORMANCE EXPECTATIONS

BY DAY 30

• Demo volume materially increased from current baseline (~40/month)

• Outbound prospecting systems operational

• HubSpot pipeline restructured and organized

• Revenue reporting dashboard implemented

BY DAY 60

• Minimum 15–20 completed demos per week

• Minimum 30+ new paid accounts monthly run-rate

• SDR hiring process completed or actively underway

• Consistent outbound pipeline generation established

• Weekly forecasting and pipeline accountability cadence operational

BY DAY 90 — PRIMARY SUCCESS METRICS

• 200 demos scheduled monthly

• 100 completed demos monthly

• 75+ trial activations monthly

• 70%+ trial-to-paid conversion rate

• 50+ new paid accounts monthly

• $15,000+ net new MRR monthly

• 3x pipeline coverage maintained

• 4,000+ new contacts added monthly

• Forecast accuracy within 10%

• SDR & AE infrastructure operational and accountable

Performance is measured by measurable business outcomes and revenue performance, not activity alone. This role is directly accountable for completed demos, show rates, pipeline growth, trial activations, trial-to-paid conversion, new paid accounts, net new MRR, and forecast accuracy.

WHO THIS ROLE IS FOR

This role is for someone who:

• Has built outbound revenue systems from the ground up

• Understands how to create pipeline without relying on inbound marketing

• Has experience hiring, onboarding, and managing remote SDR teams

• Is comfortable with cold calling as the primary prospecting channel

• Can operate independently in a fast-moving startup environment

• Thrives under aggressive growth targets and performance expectations

• Talks in demos, show rates, conversion rates — not theory or philosophy

• Has strong English for managing US-market SDRs and reporting to founders

• Is low ego, easy to work with, and drama-free

• Prefers ownership, execution, and accountability over structure and comfort

This role is NOT for someone who:

• Depends on inbound leads or marketing-generated opportunities

• Primarily manages existing sales teams without personally driving pipeline

• Requires long ramp periods or extensive hand-holding

• Struggles with accountability, KPI management, or forecasting discipline

• Has a history of leaving roles after 6–9 months

• Is uncomfortable being measured weekly on demos, pipeline growth, and revenue

• Prefers strategy discussions over execution and measurable results

REQUIREMENTS

Must-Have:

• 5–7 years leading high-volume outbound sales teams with cold calling focus

• Proven track record managing remote SDR teams (not just in-person)

• Direct experience scaling from small team (2–3 reps) to larger operation (5+ reps)

• Demonstrable results with specific metrics: demos scheduled, show rates, conversion rates

• Hands-on execution mentality — willing to personally prospect and train reps

• Experience managing high-turnover SDR environments

• Strong English communication for managing international teams and US prospects

• SaaS sales experience with monthly recurring revenue models

• Comfort with $200–500/month contract values and transactional sales cycles

• HubSpot CRM proficiency

Nice to Have:

• Previous experience in restoration, construction, or blue-collar industries

• Background scaling teams in Latin American markets

• Experience with franchise or multi-location business models

• Track record building sales operations from scratch at startups

• Bilingual capabilities (Spanish/Portuguese + English)

COMPENSATION STRUCTURE

Base Pay: $5,000/month (open to flexibility for the right candidate) Annual New ARR Target: $2,000,000

Monthly Team KPI Performance Bonus — eligible for up to $2,000/month based on:

• 4,000+ new qualified leads sourced & entered into HubSpot per month

• SDR team: 200 demos scheduled, 50%+ show rate, 100 completed demos/month

• AE team: 75+ trial activations, 70%+ trial-to-paid conversion, 50 new paid accounts, $15,000+ in new MRR/month

2026 Milestone Bonuses (cumulative, one-time):

• $10,000 — 350 active subscriptions

• $15,000 — 450 active subscriptions

• $25,000 — 550 active subscriptions

Total upside for a strong performer: $50,000+ annually.