Head of Sales | 60550121811

Position: Head of Sales

Working hours: 9 am to 5 pm EST (Hubstaff.com login required during work hours- No Exception)

Location: Remote - Open to candidates in South Africa 

Compensation Structure

• Annual New ARR Target: $2,000,000
• Base Pay: $5,000 per month

2026 Milestone Bonuses (Cumulative, One-Time for 2026 Only)

• $10,000 at 350 active subscriptions
• $15,000 at 450 active subscriptions
• $25,000 at 550 active subscriptions

Monthly Team KPI Performance Bonus

Eligible for up to $2,000 per month based on achievement of the following KPIs:

• Minimum 4,000 new qualified leads sourced & entered into HubSpot per month
• 200 demos scheduled per month
• Minimum 50% demo show rate
• 100 completed demos per month

AE Performance

• Minimum 75 trial signups/activations
• Minimum 70% trial-to-paid conversion rate
• 50 new paid accounts per month
• Minimum $15,000 in new MRR generated per month

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Company Overview

We are a fast-growing SaaS company transforming how franchise systems and restoration companies manage accounts receivable and collections.

We help multi-location operators and franchise organizations:

• Accelerate cash flow
• Reduce 60, 90, and 120+ day AR aging
• Automate collections workflows
• Standardize follow-up across every location
• Give leadership real-time visibility into company-wide AR performance

Most restoration companies and franchise operators still manage collections manually through spreadsheets, disconnected systems, phone calls, and inconsistent follow-up processes. The result is slow collections, poor visibility, operational inefficiency, and millions of dollars trapped in accounts receivable.

Our platform solves that problem by combining automated collections workflows, integrated payment systems, centralized reporting, and real-time visibility into receivables performance across an entire organization.

The market demand is real and the pain point is massive; customers are actively paying for the product today. We are already working with restoration companies, franchise operators, and multi-location businesses that rely on our platform to improve cash flow and operational efficiency.

We are now entering a major growth phase focused on scaling outbound sales, expanding franchise relationships, and building a world-class revenue organization. This is an opportunity to help build the revenue engine at an early-stage company with a real product, a proven market problem, and significant growth potential.

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

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Core Responsibilities & Revenue Accountability

The Head of Sales is responsible for building and scaling our outbound revenue operation from the ground up. This is a highly hands-on leadership role focused on outbound pipeline generation, demo production, SDR team development, CRM management, forecasting discipline, and revenue growth execution.

This is not a management-only position. The Head of Sales is expected to actively participate in outbound execution, sales process optimization, pipeline management, and revenue accountability on a daily basis.

Primary Responsibilities Include:

• Outbound Systems: Building and managing outbound prospecting systems.
• Lead Sourcing: Sourcing and organizing qualified target accounts, and creating and maintaining outbound lead lists.
• CRM & Pipeline Management: Managing lead flow, pipeline structure, and CRM accuracy within HubSpot, as well as assigning and distributing leads across SDRs and Account Executives.
• Team Development: Recruiting, onboarding, training, and managing SDR personnel while establishing outbound activity standards and KPI accountability.
• Conversion Optimization: Increasing demo volume, trial activations, and paid account conversions.
• Sales Execution: Improving outbound messaging, positioning, and sales execution while implementing structured forecasting, reporting, and weekly revenue accountability.
• Scalability: Building scalable outbound systems capable of supporting long-term company growth.

• Current Baseline: Current demo volume is approximately 2–3 demos per week. The expectation for this role is to scale outbound production to a minimum of 25+ completed demos per week within the first 90 days while building the infrastructure necessary to support continued growth beyond that level.
• 100% Outbound Environment: This is a 100% outbound sales organization. There is currently no significant inbound lead flow, paid marketing engine, or existing SDR infrastructure generating qualified opportunities.
• The Mission: The Head of Sales is expected to create predictable revenue growth through disciplined outbound execution and operational leadership.

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Performance Metrics & Direct Accountability

Performance is measured by tangible business outcomes and revenue performance, not activity alone. This role is directly accountable for:

• Completed demos and demo show rates
• Pipeline growth
• Trial activations
• Trial-to-paid conversion rates
• New paid accounts
• Net new MRR growth
• SDR and AE performance, alongside forecast accuracy
• Overall revenue execution

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90-Day Performance & Execution Expectations

The Head of Sales is expected to rapidly build and scale the outbound revenue engine during the first 90 days.

BY DAY 30

• Demo volume materially increased from current baseline
• Outbound prospecting systems operational
• HubSpot pipeline restructured and organized
• Revenue reporting dashboard implemented
• Outbound lead sourcing and CRM management processes established

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
• 50+ new paid accounts monthly
• $15,000+ net new MRR monthly
• 3x pipeline coverage maintained
• 4,000+ new contacts added monthly
• Accurate forecasting within 10%
• SDR & AE infrastructure operational and accountable

Execution Notice: This role is heavily performance-based and requires immediate execution. Failure to materially increase demo production, pipeline growth, and new paid account generation within the first 60 days may result in reevaluation or termination of the contractor relationship.

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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
• Is comfortable sourcing leads, building outbound processes, and driving consistent demo volume
• Has experience hiring, onboarding, and managing SDR teams
• Understands pipeline math, forecasting, and sales accountability
• Can operate independently in a fast-moving startup environment
• Thrives under aggressive growth targets and performance expectations
• Prefers ownership, execution, and accountability over structure and comfort

This role is not for someone who:

• Primarily manages existing sales teams without personally driving pipeline
• Depends on inbound leads or marketing-generated opportunities
• Requires long ramp periods or extensive handholding
• Avoids outbound prospecting or enterprise-level sales conversations
• Struggles with accountability, KPI management, or forecasting discipline
• Is uncomfortable being measured weekly on demos, pipeline growth, and revenue performance
• Prefers strategy discussions over execution and measurable results

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To move forward successfully share the following to Sammy@somewhere.com :

• A short cover letter:

1.  Explaining why you would be a strong fit for the role. Use this as an opportunity to pitch yourself directly to the client by highlighting your relevant experience, achievements, and motivation for applying.
2. Include the reasons for leaving your last 3 roles and share your long-term career plans. We value long-term commitment and want to ensure a stable, mutually beneficial working relationship going forward.

• What is your notice period?
• An updated CV. Ensure it highlights your key skills and experience you have relevant to the role.
• A video introduction link where you introduce yourself and summarize your experience and key achievements. You don’t need to mention the specific role you are applying for—keep it general by highlighting your background, expertise, and what you can bring to your next role. Use Google Drive and ensure that the link is unrestricted, viewable by anyone with the link and does not expire. Ensure your full name or contact details are not visible on this public link.

Tips for a professional, well-presented video:

• Record in a quiet, well-lit space 
• Dress professionally, as you would for an interview.
• Do not read from a script 
• Ensure your device is fixed and stable
• Here are some examples should you need it: https://www.youtube.com/@somewheredotcom/shorts