Director of Sales

About the Role

We are looking for a highly driven Director of Sales to lead and scale our B2B sales organization. In this role, you will be a working leader—developing strategy, coaching Sales Managers, and stepping in alongside them when needed to drive performance.

Your mission is to build and optimize a team that sells digital marketing solutions (software services) to small and mid-size businesses, particularly in the services industry. You will help shape the strategy, execution, and operational rigor of the sales organization, using data and analytics to accelerate revenue growth.

About Olly Olly

Olly Olly is a $25M ARR digital marketing company with 350 employees helping small, local businesses grow without becoming marketers. We're transitioning from a website-plus-marketing-tools platform into an intelligent growth operating system—built on the philosophy that marketing should be automatic, not accidental.

Key Responsibilities

• Lead, mentor, and develop Sales Managers and their teams, providing hands-on coaching, deal support, and performance management.
• Build and refine scalable sales processes in conjunction with sales leadership, workflows, and territory strategies for a high-velocity, transactional B2B sales environment.
• Define, monitor, and report on critical sales KPIs, including conversion rates, pipeline health, velocity, and revenue performance.
• Develop accurate sales forecasts, performance monitoring and projection strategies in collaboration with Revenue Operations.
• Ensure effective use of HubSpot CRM for pipeline tracking, reporting, automation, and process compliance.
• Support the company’s transition into a SaaS-first model by aligning processes, training, and team structure around a hybrid product and services offering.
• Onboard, and develop top sales talent to build a high-performing, scalable team.
• Build and run leadership development programs to uplevel managers and build rep bench strength
• Establishes best practice and process for ongoing coaching and development including call breakdowns and sales skill training
• Partner with recruiting to develop and administer recruiting and hiring onboarding process
• Partner with rev ops and leadership to create motivation/contest strategies to drive performance
• Support the building of culture and values

Required Qualifications

• 5 years of sales leadership experience, including managing Sales Managers.
• Proven success in transactional B2B sales environments with high-volume deal cycles.
• Strong operations background, with experience creating or optimizing processes and systems.
• Highly data-centric with strong analytical skills; comfortable building dashboards, reports, and forecasting models.
• Experience selling digital marketing solutions such as SEO, PPC, websites, or lead-generation tools.
• Experience working with SMBs, ideally within the home services sector (contractors, trades, local service providers).
• Hands-on experience with HubSpot CRM, including reporting, pipeline management, and automation.
• Excellent coaching, communication, and leadership skills with a willingness to roll up your sleeves.

Preferred Experience

• Experience scaling a sales organization during a services-to-SaaS transformation.
• Background in operations, revenue operations, or sales enablement.
• Experience with sales playbook development and structuring compensation or incentive programs.
• Familiarity with home services business operations and buying behaviors.
• Experience with multichannel sales strategies (phone, email, inbound/outbound).

What We Offer

• Competitive salary and performance-based incentives
• Comprehensive benefits package (medical, dental, vision, etc.)
• Generous PTO and paid holidays
• High-impact role with direct influence on company strategy and revenue growth

Why Join Us

We’re in an exciting period of transformation—from a service-driven agency to a SaaS-forward, technology-focused company. As Director of Sales, you will play a key role in shaping our sales strategy, mentoring the next generation of sales leaders, and directly contributing to our growth. Your work will help thousands of small businesses grow, operate more efficiently, and reach new levels of success.

Diversity and Inclusion at Olly Olly

At Olly Olly, we celebrate differences because diversity drives innovation, and your voice truly matters here. As we shape the future of small business growth together, it's important that we also comply with all U.S. employment eligibility laws. Before applying, be sure to have current, independent authorization to work in the United States and all I-9 required documentation. While we value every unique perspective, keep in mind that we're not able to offer employment visa sponsorship.