Senior Outbound Sales Manager

About the role

This is a founding role. You're not inheriting a finished motion; you're defining one. You'll lead a team of AEs both fully outbound and blended segments, own pipeline creation targets, and partner closely with RevOps and Marketing Ops to turn outbound from an activity into a measurable revenue driver.

Responsibilities

• Define and continuously evolve segmentation and targeting strategies across your two segments
• Build and refine outbound playbooks across email, phone, LinkedIn, and multi-threading
• Partner with Marketing to sharpen messaging and campaign performance
• Establish and own outbound KPIs tied to pipeline creation and downstream conversion
• Provide feedback on the technology stack to continuously improve outbound performance
• Lead event opportunities in how they drive new customer acquisition
• Own high profile local networking opportunities with additional Trainual executives (Suns, Waste Management etc)
• Own outbound pipeline generation targets and conversion metrics end-to-end
• Improve meeting quality, win rates, and deal progression across the team
• Diagnose and address gaps across targeting, messaging, rep execution, and funnel performance
• Lead a team of Account Executives across multiple motions and segments
• Full-cycle AEs cover organizations with 25–349 FTEs, balancing inbound and outbound
• Mid-Market AEs cover organizations with 350–1,000 FTEs, running 100% outbound
• Coach outbound fundamentals: personalization, sequencing, objection handling, and progression
• Drive accountability to outcomes — pipeline, conversion, and revenue — not just activity
• Partner with RevOps to build and optimize workflows, reporting, and funnel visibility in HubSpot
• Collaborate with Marketing Ops on campaign execution, targeting, and data quality
• Ensure alignment across GTM teams to improve efficiency and scalability of outbound efforts
• Own outbound infrastructure within HubSpot: sequences, workflows, and reporting
• Maintain data hygiene and build reporting that drives real decision-making
• Continuously improve processes to support a team that's growing
• Run structured tests across messaging, channels, and targeting approaches
• Use data to iterate quickly — and scale what's working

Requirements

• 3–5+ years leading outbound AE teams in a B2B SaaS environment, with a track record of hitting or exceeding pipeline and revenue targets
• Proven outbound builder — you've created or significantly evolved an outbound motion, not just managed an existing one
• Full-cycle fluency — comfortable coaching reps across every stage from cold outreach through close
• SMB and mid-market experience — you understand the nuance of selling into organizations of different sizes and complexity
• CRM discipline — hands-on experience with HubSpot (or similar), including sequences, workflows, and funnel reporting
• Cross-functional partnership — you've worked closely with RevOps and Marketing Ops and know how to get the most out of those relationships
• Data-driven — you can read funnel performance, identify what's broken, and translate insights into action

Qualifications

You're a builder who leads from the front. You've run outbound AE teams before and have the playbooks, scars, and wins to show for it. Strategy and execution aren't in tension for you — you set the direction and you're in the trenches making sure it happens. You don't wait for the motion to be handed to you. You design it, test it, and scale it.

You coach with clarity and hold the bar high. You can diagnose whether a problem lives in targeting, messaging, rep execution, or funnel design — and you know how to fix each one. You develop AEs through real coaching: personalization, sequencing, objection handling, and deal progression — not just scorecards. Your team feels accountable as a feature, not a burden.

You think in systems. HubSpot isn't just a CRM to you — it's a performance layer. You build workflows, sequences, and reporting that make the whole team faster. You're excited to build and test new tech, like AI SDRs. You partner well with RevOps and Marketing Ops because you understand what they need and what they can build together with you. You run structured experiments, learn fast, and scale what works.

Skills

• Outbound sales leadership
• CRM proficiency (HubSpot preferred)
• Strategic thinking and execution
• Team coaching and development
• Data analysis and interpretation
• System design and optimization

Benefits

This role offers an on target earnings (OTE) of $200,000. Role level and final compensation will be determined based on experience and hiring project relevant to this role and industry. It also includes stock options, benefits, and all of our brag-worthy culture perks.

Pay

This role offers an on target earnings (OTE) of $200,000. Role level and final compensation will be determined based on experience and hiring project relevant to this role and industry.

Schedule

This role is expected to be in office at least 3 days per week — and you're welcome to come in more if you'd like.