[Hiring] Head of Business Development & Sales @Five Jars Corp

Role Description

We are looking for a hands-on commercial leader who can own the transition from the business development and sales side.

Key Responsibilities

• Build and Own Lead Generation
  • Develop and execute a practical lead-generation strategy across Five Jars’ service and product directions.
  • Define and refine ideal customer profiles, buyer roles, target-account criteria, and priority markets.
  • Research new industries, market segments, accounts, partners, and commercial opportunities.
  • Build targeted account lists and identify relevant decision-makers.
  • Personally execute targeted outbound activities during the initial stage of the role.
  • Develop personalized outreach through email, LinkedIn, referrals, industry communities, events, and other appropriate channels.
  • Respond to and qualify inbound leads.
  • Reactivate previous leads, stalled opportunities, former clients, and existing relationships.
  • Identify expansion opportunities within the existing client base.
  • Develop referral, technology, agency, and industry partnerships.
  • Work with the company’s marketing resource to improve landing pages, case studies, campaigns, sales materials, and inbound conversion.
  • Test different messages, offers, industries, buyer segments, and acquisition channels.
  • Track channel performance from initial contact through qualified opportunity and revenue.
  • Identify why previous lead-generation activities did or did not work.
  • Discontinue low-performing activities rather than optimizing for outreach volume.
  • Establish a repeatable lead-generation process that can later be delegated or scaled through additional hires or external resources.
• Own the Full Sales Cycle
  • Take responsibility for opportunities from initial contact through contract signature.
  • Respond to inbound leads.
  • Generate and research targeted outbound opportunities.
  • Qualify leads against agreed ICP and commercial criteria.
  • Run discovery calls.
  • Identify business goals, problems, stakeholders, budget, timeline, and decision process.
  • Shape the commercial solution.
  • Prepare proposals, estimates, presentations, and follow-up materials.
  • Handle objections and negotiations.
  • Maintain momentum and clear next steps.
  • Progress opportunities through to close.
• Rebuild the Business Development and Sales Process
  • Review the existing commercial process and identify where opportunities are being lost.
  • Audit recent leads, proposals, and lost opportunities.
  • Conduct win/loss analysis.
  • Identify weaknesses in qualification, discovery, positioning, pricing, proposals, follow-up, or trust-building.
  • Define clear sales stages and exit criteria.
  • Establish practical lead qualification rules.
  • Improve CRM data quality and forecasting.
  • Create reusable discovery, proposal, follow-up, and presentation templates.
  • Define appropriate sales KPIs.
  • Ensure that qualified opportunities are consistently progressed.
• Help Transform Five Jars’ Go-to-Market Direction
  • Work with company leadership to refine what Five Jars sells and how those services are presented to the market.
  • Analyze demand across existing and adjacent markets.
  • Identify commercially attractive project types.
  • Help shift positioning away from technology-specific messaging such as Drupal or WordPress.
  • Develop offers around products, integrations, digital platforms, automation, and managed services.
  • Help package services into clearer and easier-to-buy engagements.
  • Evaluate pricing, scope, commercial structure, and differentiation.
  • Test new service propositions with real prospects.
  • Recommend which verticals and opportunities Five Jars should prioritize or avoid.
• Develop Revenue Channels
  • Build a balanced commercial pipeline using channels appropriate for a specialized software and digital product company.
  • Potential channels include:
    • Inbound lead conversion.
    • Expansion of existing accounts.
    • Reactivation of previous leads and opportunities.
    • Targeted account-based outreach.
    • Strategic partnerships.
    • Referrals.
    • Technology ecosystems.
    • Industry events and conferences.
    • Selective outbound campaigns.
    • Product-led entry opportunities.
• Develop Existing Accounts
  • Work with current Five Jars clients to identify additional opportunities, including:
    • Integrations.
    • Platform modernization.
    • New digital products.
    • Automation.
    • AI-enabled functionality.
    • Mobile or self-service experiences.
    • Accessibility and performance improvements.
    • Ongoing managed services.
    • Screen Pulse or Deyra adoption.
• Sell Five Jars Products
  • Own or support the commercial development of Screen Pulse and Deyra.
  • Understand the products and target customers.
  • Run product discovery and demonstrations.
  • Qualify product opportunities.
  • Prepare commercial proposals.
  • Independently close straightforward product deals.
  • Identify opportunities to bundle products with Five Jars services.
  • Collect market feedback.
  • Help refine pricing, packaging, positioning, and target segments.
  • Distinguish real customer demand from speculative product ideas.
• Build the Future Commercial Team
  • Initially, this is a hands-on individual contributor position.
  • As the commercial process becomes repeatable, you will be expected to:
    • Identify which additional sales or marketing capabilities are genuinely needed.
    • Define future roles and responsibilities.
    • Participate in hiring.
    • Onboard and manage commercial team members.
    • Establish performance expectations.
    • Create a structure that does not depend indefinitely on the founders.

Qualifications

• Proven experience owning the complete B2B sales cycle for custom software development, digital products, systems integration, digital agencies, or related professional services.
• Experience personally generating, qualifying, progressing, and closing opportunities.
• Experience selling services to clients in the United States.
• Demonstrable history of closing mid-market service or technology deals, not only low-cost SaaS subscriptions.
• Strong experience running business-focused discovery calls.
• Ability to translate client problems into a clear commercial solution.
• Experience preparing proposals, statements of work, estimates, presentations, and follow-up materials.
• Experience responding to RFPs.
• Experience handling objections, negotiations, and complex decision processes.
• Ability to work with technical teams and understand software delivery sufficiently to sell it credibly.
• Experience improving or building sales processes in an environment where they were incomplete or ineffective.
• Ability to work independently without requiring daily management from founders.
• (If candidate is not English-native speaker) Strong written and spoken English, C1–C2.
• Strong organizational discipline and CRM usage.
• Ability to work hands-on before building or managing a team.
• Comfortable working in an organization with limited marketing and sales resources.

Requirements

• Strongly Preferred:
  • Experience selling both professional services and software products.
  • Experience selling digital product development, integrations, portals, platforms, SaaS, or managed services.
  • Experience creating or rebuilding a business development function.
  • Existing relationships or experience in nonprofit, membership, healthcare, fitness, cultural, education, or association markets.
  • Experience with HubSpot.
  • Experience developing referral and technology partnerships.
  • Familiarity with CMS, CRM, API, cloud, and integration projects.
  • Experience with account-based and targeted outbound sales.

Benefits

• Full-time remote work.
• Contract in the first year; employment with access to all company benefits afterwards.
• Fixed compensation plus performance-based commission.
• Significant ownership of the commercial function.
• Direct access to company leadership.
• Opportunity to influence the company’s future direction.
• Support for professional development and relevant industry events.