Director of Outbound Sales & Automation

LeadVenture is looking for a Director of Outbound Sales and Automation to join our Thumbstopper team. As the Director of Outbound Sales and Automation at ThumbStopper, you own the top of the sales funnel. You lead a small, high-output outbound team while staying hands-on in the work yourself. You build and run an AI-assisted outreach engine that turns targeted account research into booked meetings and demoed leads for the sales team.

This is a player and coach role. You set the outbound strategy, coach two SDRs, and personally generate pipeline alongside them.

The core of the team’s strategy is the documented, proven “top down” approach. Outreach starts with senior decision makers and works down to the right buyer, which builds credibility, earns internal referrals, and shortens the path to a booked meeting. You pair this approach with a modern sales tech stack to position ThumbStopper’s value to brand marketing leaders and book the meetings that fuel revenue.

Team Performance Targets

• 35+ booked meetings per month across the team
• 25+ Sales Demoed Leads (SDLs) per month resulting from those meetings
• Individual pipeline contribution as a working member of the team, not only a manager
• Targets set with the Chief Revenue Officer and adjusted as the team scales

Supervisory Responsibilities

Sales Development Representatives (2)

Job Duties / Responsibilities

• Operate as a player and coach. Personally run outbound to generate meetings while leading and developing the SDR team to hit a combined goal of 35+ booked meetings and 25+ SDLs per month.
• Run the “top down” approach. Make the “top down” method the core of the team’s outbound strategy. Open accounts at the senior decision maker level and work down to the right buyer, using executive conversations and internal referrals to get in faster.
• Build the outbound engine. Create, document, and continuously improve a repeatable playbook across calls, email, and social, using AI to draft, personalize, and automate outreach at scale.
• Own the outbound tech stack. Get full value from every tool in the stack.
• Put AI to work. Use AI tools to research accounts, write first-draft messaging, build and refine sequences, summarize calls, and remove manual busywork so the team spends more time in live conversations.
• Build and prioritize targeted account lists within ThumbStopper’s core verticals: powersports, outdoor power equipment, marine, construction and industrial, and RV, as well as aggressively expanding into the many untapped and emerging ICP fit verticals.
• Run discovery conversations with brand marketing leaders such as CEO, CRO, VP of Sales, VP of Marketing, CMO, and Director of Marketing, qualify fit, and clearly position ThumbStopper’s value.
• Create, implement, and manage the operational and strategic metrics that drive performance, including:
• Operational
• Calls to connects to conversations to booked meetings
• Email open and reply rates, and sequence performance by step
• Connect rates and talk time from the dialer
• Lead source effectiveness, so effort goes where it converts
• Strategic
• Booked meetings and SDLs per month
• Total pipeline sourced by the team
• Show rate and meeting to SDL conversion
• Closed business from SDR-sourced opportunities
• Coach to the numbers. Run regular call reviews, message reviews, and pipeline reviews that raise individual and team output.
• Respond quickly to inbound interest and convert it into booked meetings.
• Overcome objections and connect ThumbStopper’s value to each prospect’s real needs.
• Keep Salesforce clean and current, with accurate logging of activities, leads, opportunities, and accounts.
• Partner with marketing on outbound sales materials as needed.
• Prepare for and lead weekly team meetings and pipeline reviews.
• Stay current on outbound best practices and emerging AI sales tools and bring the best of them into the team’s workflow.
• Attend industry events identified through collaboration with the Chief Revenue Officer.

Additional duties and responsibilities as required.

Technology and AI Proficiency

• Apollo.io: prospecting, data enrichment, list building, and multi-step sequences
• Koncert: power dialing to lift connect rates and conversations per hour
• Salesforce: CRM hygiene, pipeline management, dashboards, and reporting
• Outlook: professional email and calendar management
• Claude and ChatGPT: account research, message drafting and testing, sequence creation, call summaries, and automating repetitive tasks
• Quick to learn and adopt new AI and sales tools, and able to teach the team to use them well

Daily Requirements

• Contribute a minimum of 40 working hours per week, excluding lunch and breaks.
• Participate in scheduled meetings to align on department priorities and review pipeline.
• Interact professionally with sales, marketing, customer success, and management.

Required Skills / Abilities

• 4+ years in outbound sales development, with 2+ years leading or mentoring SDRs or a high-volume outbound team
• Proven track record of personally generating pipeline and leading a team to hit or beat meeting and pipeline goals
• Experience running a “top down” outbound approach, starting at the executive level and working down to the buyer
• Hands-on fluency with a modern sales tech stack, including a prospecting platform (Apollo.io or similar), a sales dialer (Koncert or similar), and Salesforce
• Practical experience using AI tools such as Claude or ChatGPT to research, write, and automate outreach
• Strong business sense and curiosity: you know your buyer, their business, and what ThumbStopper means to their success
• Excellent verbal and written communication skills
• Coaching mindset with the ability to develop talent and raise team output
• Team oriented, with a history of collaborating across functions in a fast-paced environment
• Competitive, high energy, organized, and detail oriented
• Self-motivated, with the resilience to find motivation in temporary setbacks
• Proven ability to build and maintain relationships with prospects and clients
• Demonstrated ability to work effectively in a mixed-mode environment (onsite, remote, or hybrid), including consistent use of video conferencing, collaboration tools, and proactive communication while maintaining a professional on-camera presence.

Preferred Qualifications

• Experience selling marketing technology or SaaS to brand marketing leaders
• Familiarity with ThumbStopper’s verticals: powersports, outdoor power equipment, marine, construction and industrial, and RV. As well as being able to identify new verticals that fit ThumbStopper’s ICP.
• Experience building outbound sequences and automations from scratch
• History of testing and rolling out new AI tools across a sales team

Compensation

• Salary range of $110,000 to $130,000, depending on experience
• 2% commission on closed deals that originated from SDR outreach
• Plus benefits per company policy

Physical Requirements

• Prolonged periods of sitting at a desk and working on a computer
• Must be able to lift up to 15 pounds at a time