Director of Sales Development

Location: On-site, Tampa, FL.

Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle.

The Role

We are seeking an experienced and results-oriented Director of Sales Development to drive our outbound sales strategy and manage the front-end of our sales funnel. This role will lead a team of two SDR Managers, who oversee in-person Sales Development Representatives (SDRs) in Tampa. The Director of Sales Development will collaborate with Sales Leadership, including Account Executives, Marketing, and Revenue Operations, to drive pipeline quality, process improvements, and alignment on sales goals. This position offers the unique opportunity to directly influence revenue growth through strategic planning, team performance optimization, and cross-functional collaboration.

Responsibilities

• Leadership & Team Management:
• Lead, mentor, and develop two SDR Managers who oversee teams of SDRs. Cultivate a high-performance culture focused on accountability, continuous learning, and hitting team targets.
• Work with the sales enablement team to create playbooks, structured training and onboarding programs, and provide ongoing coaching to SDR Managers and SDRs on sales development skills, effective outreach, and opportunity qualification.
• Sales Strategy & Execution:
• Design and execute a data-driven, multi-channel strategy to drive pipeline growth, balancing volume with quality to ensure high conversion rates.
• Partner closely with Sales Leadership, Marketing and RevOps to define target audiences, messaging, and qualification criteria. Collaborate on campaigns, initiatives, and promotional strategies that drive qualified opportunities to Account Executives.
• Monitor, track, and analyze the entire SDR funnel, identifying areas of improvement and optimizing strategies to maximize engagement and conversion rates.
• Collaboration & Alignment with Account Executives:
• Establish strong partnerships with Account Executives and Sales Leadership to ensure seamless lead handoffs and clear alignment on qualification criteria. Collaborate regularly with AEs to adjust targeting, address challenges, and share performance insights.
• Act as a strategic advisor to Sales Leadership, providing data-driven insights and feedback from SDR activities to improve messaging, targeting, and value propositions.
• Performance Management & Optimization:
• Develop and track key performance metrics for SDR Managers, individual SDRs, and the overall sales development function. Use data and KPIs to assess team effectiveness, identify improvement areas, and implement strategies to enhance productivity and results.
• Regularly conduct deep-dive performance analysis, identifying bottlenecks or trends in SDR outreach, and implementing corrective actions or enhancements to the team’s processes.
• Process & Technology Improvements:
• Work with Revenue Operations to optimize CRM workflows, sales enablement tools, and SDR outreach technology. Identify and recommend technology solutions that enhance SDR efficiency and accuracy, from automated prospecting tools to engagement platforms.
• Work with Revenue Operations to define workflows, scripts, and outreach cadences to ensure SDRs operate at peak effectiveness, continuously adapting based on market trends, campaign effectiveness, and SDR feedback.
• Team Culture & Engagement:
• Foster a collaborative and supportive team environment that prioritizes growth, accountability, and success. Champion a culture of feedback, motivation, and open communication.
• Plan and facilitate regular team meetings, one-on-ones, and performance reviews, ensuring all team members have the guidance, recognition, and resources they need to succeed.

• 5+ years of experience in sales development or business development, with a minimum of 3 years in a leadership role overseeing SDR teams or managers.
• Demonstrated success in building and scaling SDR teams, with a proven ability to develop high-performing sales development processes.
• Expertise in pipeline generation, SDR funnel management, and leveraging metrics to drive continuous improvement.
• Strong knowledge of CRM systems (Salesforce preferred), sales engagement platforms, and sales technology stacks.
• Exceptional leadership, communication, and problem-solving skills, with the ability to thrive in a fast-paced, high-growth environment.

We care deeply about making Ottimate an incredible place to work and invest a significant amount of time and energy into creating and maintaining a company culture that provides our team with a generous level of support whilst inspiring them to do their best work.

The specific benefits/perks we offer are continually evolving, but currently include:

• Salary range: $145,000-150,000 per year plus bonusb compensation.
• Medical, Dental, Vision and other Company-Subsidized Benefits for you and your family.
• Employer sponsored 401(k) with company match.
• Paid Time Off (and the encouragement to use it).
• Annual company retreats.
• Promote from within philosophy.
• Beyond the tangible benefits though:

You will be part of a growing team, at a pinnacle moment of scale for the business, and experience the excitement of working in a startup where each action makes a huge difference.

You will have the agency to solve difficult problems creatively, the freedom to explore work that inspires you, and infrastructure to ensure you're constantly challenged and developing.

You will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution.

Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to none.

We are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural Networks.

Our leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growth.

We truly love what we do and who we do it with - and we think you will too!

Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply. Nothing in this job posting should be construed as an offer or guarantee of employment.