Director, Sales Development Representatives

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 a strategic and results-driven Director of Sales Development Representatives to lead our top-of-funnel pipeline generation. In this role, you will scale our SDR team, refine our outbound and inbound prospecting motions, and build a metrics-driven engine that consistently delivers high-quality leads to our Account Executives. You will act as the bridge between Marketing, Sales, and Revenue Operations. This is a remote work position / hybrid position, with 3 days per week in our Nashua, NH headquarters. Responsibilities Team Leadership & Development: Recruit, hire, train, and mentor a high-performing team of SDRs and SDR Managers. Pipeline Generation: Develop and execute strategies to fill the sales pipeline with qualified leads, ensuring conversion rates and revenue targets are consistently met or exceeded. Process Optimization: Continuously iterate on outreach techniques, call scripts, email cadences, and qualification criteria. Cross-Functional Alignment: Partner closely with Marketing to ensure lead quality and campaign effectiveness, and with Sales Leadership to align lead-to-opportunity handoff processes. Metrics & Analytics: Track key performance indicators (KPIs) such as activities per rep, lead-to-opportunity conversion rates, and pipeline value. Provide routine reports to executive management. Tech Stack Management: Evaluate, adopt, and optimize sales engagement and automation tools (e.g., Salesforce, LinkedIn Sales Navigator, ZoomInfo). Requirements Experience: 5+years of experience in B2B sales or business development, with at least 3+ years in a management or leadership role. Proven Track Record: Demonstrated success in building, scaling, and managing inside sales or SDR teams that hit or exceed quota. Sales Methodologies: Deep understanding of modern sales motions, including Account-Based Marketing (ABM), outbound prospecting, and inbound lead qualification. Tool Proficiency: Strong operational knowledge of CRMs (like Salesforce or HubSpot) and modern sales engagement tools. Communication Skills: Excellent written and verbal communication skills, with the ability to influence cross-functional teams. Education: Bachelor’s degree in Business, Communications, or a related field (or equivalent professional experience) 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 $150,000 to $180,000 OTE annually, and 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.