Head of Business Development and 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 10 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 work includes digital products and platforms, custom integrations, portals and self-service experiences, web and mobile applications, managed services, and our own SaaS products, Screen Pulse and Deyra.
We are now evolving our commercial direction, with a stronger focus on digital products, integrations, platforms, automation, managed services, and recurring product revenue.
We are looking for a hands-on commercial leader who can take ownership of this transition from the business development and sales side.

The Role
This is not a traditional sales management position.
Initially, you will be the primary individual contributor responsible for business development, sales, and presales. You will personally generate and qualify opportunities, run discovery calls, prepare proposals, negotiate, follow up, and close deals.
At the same time, you will help rebuild and improve Five Jars’ commercial function, identify what works, refine our positioning and target markets, establish repeatable acquisition channels, and eventually build a small sales and business development team.
The core mission of the role is simple: build a practical and repeatable commercial function that consistently creates qualified opportunities and converts them into revenue.

What you will do
Own both pipeline creation and sales conversion, from initial outreach or inbound inquiry through contract signature.
Build and execute a focused lead-generation strategy across outbound, inbound, referrals, partnerships, previous opportunities, existing clients, events, and other relevant channels.
Define and refine ICPs, buyer personas, target accounts, priority markets, and qualification criteria.
Run business-focused discovery calls, identify client needs, stakeholders, budgets, timelines, and decision processes, and translate them into clear commercial solutions.
Prepare proposals, estimates, presentations, follow-ups, and commercial materials, and independently close straightforward opportunities.
Lead larger and more complex opportunities, involving founders or technical specialists when their input is needed.
Review Five Jars’ existing sales process, CRM pipeline, proposals, lost opportunities, and lead sources, and identify where opportunities are being lost.
Improve qualification, discovery, sales stages, CRM discipline, forecasting, follow-up, sales materials, and commercial KPIs.
Work with company leadership to refine Five Jars’ go-to-market direction, service packaging, positioning, pricing, target industries, and commercial messaging.
Develop existing client accounts through consultative conversations around integrations, modernization, digital products, automation, AI-enabled functionality, managed services, and other relevant opportunities.
Support the commercial development of Five Jars’ SaaS products, Screen Pulse and Deyra, including discovery, demos, proposals, closing, and market feedback.
Develop referral, technology, agency, and industry partnerships.
Work closely with marketing, delivery, engineering, and company leadership.
Over time, identify which commercial capabilities should be added, participate in hiring, and build and manage the future commercial team.

What we are looking for
Strong experience owning the complete B2B sales cycle in custom software development, digital products, systems integration, digital agencies, or related professional services.
Proven experience personally generating, qualifying, progressing, and closing opportunities.
Strong track record selling services to clients in the United States.
Experience closing mid-market technology or professional services deals, not only low-cost SaaS subscriptions.
Strong discovery, negotiation, objection-handling, and closing skills.
Experience preparing proposals, statements of work, estimates, presentations, and RFP responses.
Ability to understand software delivery well enough to communicate credibly with both business and technical stakeholders.
Experience building or improving sales and business development processes in an environment where the function was not yet fully established.
Strong CRM discipline and ability to work with pipeline data and forecasting.
Ability to operate independently without extensive day-to-day involvement from founders.
A hands-on mindset. You should be comfortable doing the work yourself before building a team around it.
Strong written and spoken English, C1-C2 level for non-native speakers.
Based in Europe or the US, with meaningful overlap with US Eastern Time business hours.

Strong plus
Experience selling both professional services and software products, building business development functions, working with HubSpot, developing partnerships, or selling digital products, integrations, portals, platforms, SaaS, or managed services.
Experience or existing relationships in nonprofit, membership, healthcare, fitness, cultural, education, or association markets would also be valuable.

This role may be a strong fit if you are someone who
Is commercially ambitious but realistic, comfortable with ambiguity, proactive, self-directed, and able to make decisions without waiting for detailed instructions.
You care more about qualified pipeline and revenue than outreach volume or vanity metrics. You are comfortable challenging assumptions, testing new approaches, and building structure without creating unnecessary bureaucracy.
You should also genuinely enjoy being hands-on. This is not a role where proposals, follow-ups, outreach, or discovery are delegated to an existing sales team from day one.

What you will have
You will have access to Five Jars’ existing clients, case studies, proposals, HubSpot data, historical opportunities, and previous commercial efforts.
You will work directly with company leadership and receive technical support from delivery and engineering specialists for complex opportunities. You will also have support from the existing marketing resource for website, content, campaigns, and sales materials.
You will have significant ownership of the commercial function and the opportunity to influence sales processes, service packaging, positioning, commercial tools, and future go-to-market direction.
Once a repeatable commercial model is established, you will have the opportunity to build the future sales and business development team.

What we offer
Full-time remote work.
Fixed compensation plus performance-based commission with no artificial earning ceiling.
Significant ownership and autonomy in building the commercial function.
Direct access to company leadership.
Opportunity to influence Five Jars’ future commercial direction.
Paid vacation, sick leave, and public holidays.
Professional development and support for relevant industry events.
Flexible working hours with required overlap with US business hours.