Head of Business Development & Sales

About Five Jars

Five Jars is a US-based digital product and engineering company with a distributed team across the United States and Europe.

For nearly ten years, we have designed, built, integrated, and supported complex digital platforms for nonprofit organizations, membership-based organizations, cultural institutions, healthcare organizations, and other mid-market clients.

Our experience includes:

• digital platforms and customer-facing products;
• CMS-based ecosystems;
• custom integrations;
• portals and self-service experiences;
• web and mobile applications;
• managed support and platform development;
• our own SaaS products, Screen Pulse and Deyra.

We are now evolving our commercial direction. While web development remains part of our business, we intend to place greater emphasis on digital products, integrations, platforms, automation, managed services, and recurring product revenue.

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

Key Responsibilities

1. Build and Own Lead Generation

Develop and execute a practical lead-generation strategy across Five Jars’ service and product directions.

Responsibilities include:

• defining and refining ideal customer profiles, buyer roles, target-account criteria, and priority markets;
• researching new industries, market segments, accounts, partners, and commercial opportunities;
• building targeted account lists and identifying relevant decision-makers;
• personally executing targeted outbound activities during the initial stage of the role;
• developing personalized outreach through email, LinkedIn, referrals, industry communities, events, and other appropriate channels;
• responding to and qualifying inbound leads;
• reactivating previous leads, stalled opportunities, former clients, and existing relationships;
• identifying expansion opportunities within the existing client base;
• developing referral, technology, agency, and industry partnerships;
• working with the company’s marketing resource to improve landing pages, case studies, campaigns, sales materials, and inbound conversion;
• testing different messages, offers, industries, buyer segments, and acquisition channels;
• tracking channel performance from initial contact through qualified opportunity and revenue;
• identifying why previous lead-generation activities did or did not work;
• discontinuing low-performing activities rather than optimizing for outreach volume;
• establishing a repeatable lead-generation process that can later be delegated or scaled through additional hires or external resources.

The objective is to create a consistent flow of qualified opportunities – not simply contact lists, email volume, booked meetings, or other activity metrics.

2. Own the Full Sales Cycle

Take responsibility for opportunities from initial contact through contract signature.

This includes:

• responding to inbound leads;
• generating and researching targeted outbound opportunities;
• qualifying leads against agreed ICP and commercial criteria;
• running discovery calls;
• identifying business goals, problems, stakeholders, budget, timeline, and decision process;
• shaping the commercial solution;
• preparing proposals, estimates, presentations, and follow-up materials;
• handling objections and negotiations;
• maintaining momentum and clear next steps;
• progressing opportunities through to close.

You will be expected to independently close standardized and lower-complexity opportunities without requiring a founder to participate in every call.

3. Rebuild the Business Development and Sales Process

Review the existing commercial process and identify where opportunities are being lost.

Responsibilities include:

• auditing recent leads, proposals, and lost opportunities;
• conducting win/loss analysis;
• identifying weaknesses in qualification, discovery, positioning, pricing, proposals, follow-up, or trust-building;
• defining clear sales stages and exit criteria;
• establishing practical lead qualification rules;
• improving CRM data quality and forecasting;
• creating reusable discovery, proposal, follow-up, and presentation templates;
• defining appropriate sales KPIs;
• ensuring that qualified opportunities are consistently progressed.

The objective is not to introduce unnecessary sales bureaucracy. The objective is to create a process that is visible, manageable, and repeatable.

4. 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.

This includes:

• analyzing demand across existing and adjacent markets;
• identifying commercially attractive project types;
• helping shift positioning away from technology-specific messaging such as Drupal or WordPress;
• developing offers around products, integrations, digital platforms, automation, and managed services;
• helping package services into clearer and easier-to-buy engagements;
• evaluating pricing, scope, commercial structure, and differentiation;
• testing new service propositions with real prospects;
• recommending which verticals and opportunities Five Jars should prioritize or avoid.

5. 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.

The goal is not simply to maximize outreach volume. The goal is to identify channels that generate qualified opportunities and can become repeatable.

6. 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.

This should be done as consultative account development, not aggressive upselling.

7. Sell Five Jars Products

Own or support the commercial development of Screen Pulse and Deyra.

Responsibilities include:

• understanding the products and target customers;
• running product discovery and demonstrations;
• qualifying product opportunities;
• preparing commercial proposals;
• independently closing straightforward product deals;
• identifying opportunities to bundle products with Five Jars services;
• collecting market feedback;
• helping refine pricing, packaging, positioning, and target segments;
• distinguishing real customer demand from speculative product ideas.

Product sales are part of the role, but not expected to operate as a completely separate sales organization from day one.

8. 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.

Hiring a team is not the first objective. The first objective is proving a working commercial model.

Required Experience

Must Have

• 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.
  

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.

We Offer

• 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.