Strategic Account Executive Mid West

Strategic Account Executive

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 a high-performing, hunter-oriented Strategic Account Executive with a strong background in Managed Services Provider (MSP) sales to accelerate growth within Rightworks' Business Solutions organization. The ideal candidate has a proven track record of selling managed IT services, cybersecurity solutions, cloud infrastructure, Microsoft 365 services, backup and disaster recovery, compliance solutions, and recurring managed service agreements to small and midsized businesses (SMBs). This individual understands how to uncover business challenges, assess technology risks, and position managed services that improve security, productivity, operational efficiency, and business continuity. This role is responsible for acquiring new customers and expanding existing customer relationships across the Rightworks portfolio of managed IT, cybersecurity, cloud, Microsoft, compliance, productivity, and AI solutions. Success will be measured through a combination of new logo acquisition, managed services revenue growth, expansion revenue, cross-sell performance, product attachment rates, and overall customer lifetime value growth. The Account Executive will serve as a trusted advisor to SMB owners, executive leaders, operations teams, finance leaders, and technology decision-makers. The successful candidate will help organizations modernize their technology environments, strengthen cybersecurity defenses, improve compliance, reduce operational risks, and enable scalable growth through Rightworks solutions. While new customer acquisition is a primary responsibility, this role also carries significant accountability for growing existing customer relationships through strategic account expansion and cross-selling. The Account Executive will identify opportunities to attach complementary services such as cybersecurity, Managed Microsoft, cloud hosting, compliance solutions, AI-powered productivity tools, and additional managed services that help customers operate more securely and efficiently. This position combines the discipline of a traditional MSP sales professional with the ability to sell an expanded portfolio of cloud, cybersecurity, Microsoft, compliance, productivity, and AI solutions. The ideal candidate will demonstrate expertise in consultative MSP selling, recurring revenue growth, solution bundling, and long-term account development within the SMB market This is a remote work position OR a hybrid position with 3 days per week in our Nashua, NH headquarters.

Responsibilities

• New Business Development
• Identify, prospect, qualify, and close new SMB customers for managed services, cybersecurity, Microsoft, cloud, compliance, and productivity solutions.
• Develop opportunities through outbound prospecting, inbound leads, referral networks, business associations, partner channels, and SMB-focused verticals.
• Build and maintain a healthy sales pipeline using Salesforce and approved sales engagement tools.
• Conduct consultative discovery to uncover technology pain points, cybersecurity gaps, operational inefficiencies, business continuity concerns, compliance needs, and modernization opportunities.
• Manage the full sales cycle from lead generation and discovery through proposal, negotiation, close, and handoff to onboarding or service delivery teams.
• Position managed IT, cybersecurity, Microsoft 365, cloud hosting, backup/disaster recovery, compliance, and productivity solutions around measurable business outcomes.
• Sell recurring managed service agreements and solution bundles that create durable MRR/ARR growth.
• Collaborate with solution architects, sales engineers, vCIO resources, and service delivery teams to scope accurate solutions and implementation expectations.
• Develop compelling proposals, quotes, presentations, and business cases tailored to SMB priorities and buying committees.
• Translate technical capabilities into clear outcomes for CEOs, CFOs, COOs, business owners, IT leaders, and operations stakeholders.
• Own cross-sell and expansion opportunities within assigned accounts and customer segments
• Develop account growth plans that identify opportunities to expand customer adoption across the Rightworks portfolio.
• Position complementary offerings such as Business Security, Total Security, Managed Microsoft, Cloud Hosting, Cloud Protect, WISP Compliance, Transaction Pro, Spark AI, and related services.
• Partner with Customer Success, Account Management, Marketing, Solution Engineering, and Service Delivery teams to identify upgrade, modernization, expansion, and attach-rate opportunities.
• Drive conversion of customers from point solutions to broader managed services and platform adoption.
• Execute security, Microsoft 365, cloud modernization, compliance, AI, and productivity-focused account reviews that surface additional customer needs.
• Achieve cross-sell, expansion revenue, and product attach-rate objectives in addition to new logo acquisition targets.
• Develop relationships within SMB communities, business associations, referral networks, chambers of commerce, industry groups, and relevant vertical communities.
• Represent Rightworks at industry events, partner meetings, business networking forums, and SMB-focused conferences.
• Identify target verticals where managed IT, cybersecurity, Microsoft, compliance, cloud, and productivity solutions create strong business value.
• Monitor competitive dynamics, customer buying trends, and SMB market signals that may influence messaging, packaging, or go-to-market execution.
• Consistently achieve monthly, quarterly, and annual bookings targets.
• Maintain accurate forecasting, pipeline hygiene, and opportunity management.
• Report clearly on pipeline activity, conversion, revenue projections, cross-sell opportunities, expansion opportunities, and attach-rate performance.
• Use disciplined sales process, follow-through, and data-driven pipeline management to create predictable performance

Requirements

• 8-10 years of successful MSP, managed IT services, cybersecurity, cloud services, Microsoft solutions, or technology solutions sales experience.
• Demonstrated success selling recurring managed services agreements and achieving MRR/ARR growth targets.
• Experience selling managed IT, Microsoft 365, cybersecurity, backup/disaster recovery, cloud hosting, compliance, and related technology services.
• Strong understanding of MSP business models, recurring revenue sales motions, service packaging, managed service agreements, solution bundling, and customer lifecycle management.
• Demonstrated success acquiring net-new SMB customers and exceeding quota.
• Experience collaborating with solution architects, sales engineers, vCIOs, technical specialists, and service delivery teams.
• Proven success selling to SMB decision-makers, including CEOs, CFOs, COOs, business owners, operations leaders, IT managers, and technology stakeholders.
• Excellent consultative selling, discovery, presentation, negotiation, and closing skills.
• Ability to translate technical services into practical business value, risk reduction, compliance improvement, productivity gains, and scalability outcomes.
• Proficiency with Salesforce and modern sales engagement tools.
• Preferred Qualifications
• Existing network within SMB communities, business associations, chambers of commerce, referral partner networks, or relevant industry verticals.
• Experience selling into professional services, healthcare, legal, manufacturing, construction, nonprofit, financial services, or other SMB-focused verticals.
• Familiarity with Microsoft 365, Microsoft security solutions, cybersecurity frameworks, compliance requirements, cloud infrastructure, and managed services delivery models.
• Knowledge of NIST, FTC Safeguards Rule, WISP requirements, CMMC, PCI-DSS, HIPAA, or other compliance and risk frameworks relevant to SMBs.
• Experience building account expansion plans and driving attach rates across security, Microsoft, cloud, compliance, and managed services offerings.
• Industry or vendor certifications such as CompTIA, Microsoft, cybersecurity, or sales methodology certifications are a plus.
• Bachelor's degree in Business, Marketing, Technology, or related field, or equivalent experience.
• Success Metrics
• New Business
• Net New MRR, Net New ARR
• Acquisition and Pipeline Creation and Coverage
• Win Rate
• Average Deal Size Growth
• Cross-Sell & Expansion
• Expansion ARR
• Cross-Sell Revenue
• Security Attach Rate
• Managed Microsoft Attach Rate
• Average Products per Customer
• Average Revenue per Account
• Customer Lifetime Value Growth
• Multi-Product Customer Growth

Strategic & Operational

• SMB Market Penetration
• Vertical Penetration
• Forecast Accuracy
• Pipeline Hygiene
• Customer Retention
• Platform Adoption

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