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. 

Job Overview

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.  

Responsibilities

Technical Discovery & Assessment 

• 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. 

Solution Design & Architecture 

• 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. 

Technical Sales Support 

• Deliver technical presentations, product demonstrations, solution workshops, and architecture discussions for prospects and customers. 

• Participate in executive briefings and translate technical recommendations into business-relevant language for CEOs, CFOs, COOs, business owners, IT leaders, and operations stakeholders. 

• Respond to technical, security, compliance, integration, and implementation questions during the sales cycle. 

• Lead technical portions of RFP/RFI responses and provide accurate documentation for complex opportunities. 

• Design and support proof-of-concept or validation activities when required. 

Scoping, Documentation & Proposal Development 

• Develop Statements of Work (SOWs), technical solution designs, implementation assumptions, Bills of Materials (BOMs), and scope documentation. 

• Assist with pricing models, recurring revenue packaging, and margin review for complex or custom opportunities. 

• Collaborate with sales, finance, vendor partners, service delivery, and technical teams to ensure proposals are accurate, complete, and commercially viable. 

• Identify scope risks, service delivery constraints, and expectation gaps before contract execution. 

• Maintain reusable templates, documentation standards, and technical sales assets where appropriate. 

Cross-Sell & Expansion Support 

• Partner with account teams to identify expansion opportunities across Managed Microsoft, Business Security, Total Security, Cloud Hosting, Cloud Protect, WISP Compliance, Transaction Pro, Spark AI, and other Rightworks offerings. 

• Support account reviews focused on security, Microsoft 365, cloud modernization, compliance, AI, productivity, and managed services adoption. 

• Help customers understand the technical and business value of broader Rightworks solution adoption. 

• Provide technical credibility during cross-sell motions and expansion conversations. 

• Support attach-rate growth by validating solution fit and removing technical objections. 

Sales-to-Service Transition 

• Ensure clean technical handoffs to onboarding, project management, engineering, and service delivery teams. 

• Provide complete implementation documentation, validated assumptions, technical requirements, and customer context. 

• Reduce post-sale implementation risk by ensuring solution scope, responsibilities, and timelines are clearly understood. 

• Support onboarding teams during project initiation when needed to preserve continuity from sales to delivery. 

Technical Leadership & Market Feedback 

• Maintain current knowledge of MSP best practices, Microsoft 365, cloud infrastructure, cybersecurity, compliance frameworks, SMB technology trends, and relevant vendor ecosystems. 

• Provide feedback to leadership on recurring technical objections, competitive gaps, packaging gaps, and service improvement opportunities. 

• Help improve messaging, sales enablement, technical documentation, and solution packaging based on field learnings. 

Requirements

• 5+ years of experience as a Sales Engineer, Solutions Engineer, Solutions Architect, Pre-Sales Consultant, Technical Account Manager, senior MSP engineer, or related technical pre-sales role. 

• Experience in an MSP, managed services, cybersecurity, Microsoft, cloud services, VAR, or IT services environment. 

• Strong understanding of Microsoft 365, Microsoft security, cloud infrastructure, endpoint management, identity and access management, cybersecurity fundamentals, backup/disaster recovery, and managed service delivery models. 

• Experience scoping managed services agreements, professional services projects, cybersecurity solutions, Microsoft services, cloud hosting, and compliance-related engagements. 

• Ability to create SOWs, solution designs, pricing assumptions, technical documentation, and sales-to-service handoff materials. 

• Ability to translate technical complexity into clear business value for non-technical executives and SMB decision-makers. 

• Strong presentation, demonstration, discovery, documentation, and cross-functional collaboration skills. 

• Experience supporting recurring revenue sales organizations and working closely with Account Executives throughout the sales cycle. 

• Familiarity with CRM, quoting/CPQ, documentation, and MSP tools such as Salesforce, ConnectWise, Autotask, IT Glue, Quotewerks, or similar platforms. 

Preferred Qualifications

• Prior hands-on experience in IT service delivery, systems administration, network engineering, cloud engineering, cybersecurity, or MSP operations before moving into a pre-sales role. 

• Microsoft, cybersecurity, cloud, networking, or MSP-related certifications such as MS-900, AZ-104, SC-900, CompTIA Network+, CompTIA Security+, CCNA, Fortinet, SentinelOne, or similar credentials. 

• Experience supporting SMB customers across professional services, healthcare, legal, manufacturing, construction, nonprofit, financial services, or other SMB-focused verticals. 

• Knowledge of NIST, FTC Safeguards Rule, WISP requirements, CMMC, PCI-DSS, HIPAA, or other compliance and risk frameworks relevant to SMBs. 

• Experience supporting cross-sell or expansion motions by identifying technical fit for additional services. 

• Bachelor's degree in Computer Science, Information Technology, Engineering, Business, or related field, or equivalent experience. 

Success Metrics 

• Technical Effectiveness:
  Technical win rate 
  Solution acceptance rate 
  Technical validation success 
  Proposal accuracy 
  Scope accuracy 
  Deployment readiness 

• Revenue Contribution:
  Influenced MRR 
  Influenced ARR 
  Cross-sell attachment rates 
  Managed Microsoft attachment rates 
  Security attachment rates 
  Expansion opportunity support 
  Assessment-to-opportunity conversion rate 

• Operational Excellence:
  Sales-to-service handoff quality 
  Reduction in avoidable scope changes 
  Customer satisfaction during pre-sales engagement 
  Quality and completeness of documentation 
  Service delivery readiness 

Eligibility Requirements  

• This role is open to US Citizens or permanent residents authorized to work in the United States. Rightworks LLC is unable to offer visa sponsorship.  

• Due to specific state regulations, we are unable to accept applications from residents of California, Hawaii, or Alaska.  

• Relocation will not be offered for this position. 

Compensation

Our Compensation range for this role ranges from a base salary of $120,000 to $150,000 annually, with a commissions package, and potential on target earnings of up to $195,000. Compensation is determined based on factors such as relevant experience, skills, and internal equity. 

Benefits  

To provide best-in-class solutions, we need a best-in-class team. We offer competitive salaries to recruit the best talent. We provide company-paid short and long-term disability insurance, life insurance and a generous 401K match. We offer highly affordable medical, dental, vision coverage, and many other valuable benefits. We offer flexible PTO, and numerous paid holidays, affording you the time to be there for what is important in your life. We encourage giving back to our communities by providing paid volunteer time off. We are proud to be an Equal Opportunity Employer! 

This job description may not be inclusive of all assigned duties, responsibilities, or aspects of the job described, and may be amended at any time at the sole discretion of the employer.