Strategic Sales Engineer

Rightworks offers the only intelligent cloud purpose-built for accounting firms and professionals. Backed by award-winning support, our fully managed IT and applications ensure customers have secure, reliable, on-demand access to their technology. We provide a curated software ecosystem that simplifies the complexity of running an accounting firm or small business, supported by a community of thought leaders, peer networks, and educational resources.

Our success is made possible by leveraging decades of specialized experience in leading accounting firms, SMBs and technology companies. Thousands of Firms and SMBs count on us to run their business every day.

We have a great team, we’re growing fast and have a winning culture based on innovation, teamwork, and mutual respect.

We are seeking an experienced Strategic Sales Engineer with a strong background in Managed Services Provider (MSP) environments to serve as the technical backbone of the Rightworks Business Solutions sales organization. This role partners closely with Strategic Account Executives throughout the sales process, helping SMB prospects and customers assess technology risks, evaluate current-state environments, define future-state requirements, and understand solutions that improve security, productivity, operational scalability, and business continuity.

The ideal candidate combines technical depth with strong business acumen and communication skills. They must be able to translate complex technical concepts into practical business outcomes and help SMB decision-makers understand how managed services, cybersecurity, Microsoft, cloud, compliance, productivity, and AI investments support growth, efficiency, risk reduction, and operational resilience. Success in this role will be measured through technical win rate, solution acceptance, technical validation success, proposal and scope accuracy, security and platform attachment rates, expansion revenue influence, deployment readiness, sales-to-service handoff quality, and overall contribution to revenue growth.

This position is ideal for a technical pre‑sales professional who enjoys working directly with business leaders, IT stakeholders, sales teams, and service delivery teams to solve complex challenges and support durable MRR/ARR growth in the SMB market.

This is a remote work position, OR a hybrid position, with 3 days per week in our Nashua, NH headquarters.

• Partner with Strategic Account Executives during discovery, qualification, and opportunity strategy activities.
• Conduct technical discovery sessions with SMB prospects and customers to assess infrastructure, Microsoft 365 environments, cloud posture, security controls, compliance requirements, operational workflows, and business continuity needs.
• Perform technical assessments, security posture reviews, and risk assessments to identify gaps, modernization opportunities, and solution fit.
• Translate business challenges into clear technical recommendations and solution options.
• Identify opportunities to attach complementary Rightworks services during discovery and assessment activities.

• Design and scope solutions across managed IT services, cybersecurity, Microsoft 365, cloud hosting, backup/disaster recovery, compliance, productivity, and AI-enabled offerings.
• Create future‑state solution recommendations that balance customer needs, technical feasibility, operational scalability, margin expectations, and service delivery readiness.
• Document assumptions, dependencies, customer responsibilities, technical prerequisites, risk areas, and implementation considerations.
• Work with service delivery and engineering teams to validate proposed architectures and reduce post‑sale implementation risk.
• Support solution bundling and platform adoption by identifying logical product combinations that solve broader customer problems.

• Deliver technical presentations, product demonstrations, solution workshops, and architecture discussions for prospects and customers.
• Participate in executive briefings and translate technical recommendations into…