Job Description - Director of Sales (SMB & Mid-Market)

Reports To: VP of Sales

Department: Sales
Location: Remote

Position Type: Full-Time

Position Summary

We are seeking an experienced sales leader who is committed to developing high-performing teams and driving sustainable revenue growth.

This role leads our SMB and Mid-Market sales teams, which have been central to our historical growth. The Director of Sales will provide day-to-day leadership for Account Executives, including coaching, training, performance management, and consistent reinforcement of strong sales execution standards.

Our inbound sales motion is strong and continues to improve. The initial priority for this leader will be to strengthen discovery, qualification, pipeline management, and forecast accuracy. Over time, this role will also help build disciplined outbound capabilities so the team can generate pipeline proactively and consistently.

The Director of Sales will report to the VP of Sales and collaborate closely with Marketing, Business Development, and Revenue Operations. Together, these teams will focus on maintaining clean data, improving forecast reliability, and building repeatable processes that scale effectively.

This position is ideal for a leader who takes pride in helping others succeed, building strong operating rhythms, and enabling the team to consistently meet and exceed its goals.

Key Responsibilities

What You'll Own

• Team performance: Own quota attainment, pipeline health, and conversion rates for the SMB and Mid-Market segments, with accountability for both team outcomes and individual performance.
• Coaching and development: Regular 1:1s, call reviews, deal strategy sessions, and skill development plans. You'll know every rep's strengths, gaps, and growth path.
• Sales process and execution: Discovery, qualification, pipeline management, forecasting, follow-up, and closing. You'll train the fundamentals, inspect them consistently, and raise the bar over time.
• Inbound conversion: Improving speed-to-lead, discovery quality, and win rates on inbound opportunities which is our highest-leverage motion today.

How You'll Lead

Success in this role requires a leadership approach that combines accountability, transparency, and active support for team development.

• Set clear expectations, maintain high standards, and address performance directly, respectfully, and consistently.
• Stay actively engaged in team success through live coaching, deal support, and meaningful participation in customer-facing opportunities.
• You tell the truth about the forecast, the pipeline, and the team, even when the truth is uncomfortable.
• Recognize team contributions while taking ownership for results and escalation needs.
• Develop team members in a way that supports career growth, internal mobility, and long-term organizational success.

Sales Process & Methodology

Candidates do not need to bring our exact playbook, but they should have a clear and adaptable approach to sales methodology and execution.

• Deep fluency in a recognized sales methodology (MEDDICC, BANT, Sandler, Challenger, SPIN, Command of the Message, or similar) and the judgment to adapt it rather than impose it.
• A clear point of view on what strong discovery and qualification look like with the ability to teach it, inspect it, and reinforce it until it's habit.
• Experience building stage definitions, exit criteria, and pipeline hygiene standards that are practical, measurable, and consistently adopted by the team.
• A forecasting discipline built on deal evidence, not solely on optimism or gut.

Who You'll Work With

• VP of Sales: Partner on strategy, segment planning, headcount, and escalations. This role will provide accurate visibility into team performance and revenue outlook while aligning on resources and priorities.
• Business Development leader & BDR team: You'll co-own the handoff. That means aligned qualification criteria, tight SLAs on follow-up, shared feedback loops on lead quality, and improving conversion of BDR-sourced opportunities into closed revenue.

Who Succeeds Here

• High character: You do what you say. Reps trust you because you're honest with them, especially when it's hard.
• Accountable: You own team and individual outcomes without excuses or blame-shifting.
• A developer of people: You have a strong track record of coaching, retaining, and advancing sales talent.

Why This Role

This role offers the opportunity to strengthen an established, high-performing sales organization with significant demand, executive support, and a team that is receptive to coaching and development.

The Director of Sales will have direct partnership with the VP of Sales, meaningful input into the continued development of the sales organization, and the ability to implement processes and standards that improve performance across the team.

For a leader who is motivated by developing people, improving process discipline, and delivering consistent revenue results, this role provides a strong opportunity to make a measurable impact.

What We're Looking For (Minimum Qualifications)

• 7+ years of B2B SaaS sales experience, including 3+ years directly managing quota-carrying Account Executives

• A track record of leading teams to consistent quota attainment

• Demonstrated success coaching and developing reps, including turning around under-performers and accelerating high performers

• Hands-on experience running pipeline reviews, forecast calls, and deal inspections in a CRM-driven environment (HubSpot experience preferred)

• Experience managing an inbound-heavy sales motion and building outbound capability

• Strong operational instincts: you create structure, rhythm, and accountability without adding friction

What We'd Be Excited to Find (Preferred Qualifications)

• Experience in SMB and Mid-Market segments with transactional-to-mid-length sales cycles

• Experience partnering with a BDR/SDR function and improving handoff conversion

• Background in vertical SaaS or selling into franchise, healthcare, or service-based industries

• Formal training or certification in a major sales methodology

• Experience at a growth-stage company where you helped scale the team and the process

Working Conditions

• Manual dexterity required to use desktop computer and peripherals.
• Utilization of software and email to perform job functions.
• Will need to conduct camera-on videoconferencing for customer calls.

Compensation and Benefits

• Competitive salary and comprehensive benefits package.
• Medical insurance premiums are covered in full for the employee (Medical, Dental and Vision)
• 401K with competitive company matching.
• Personal time off, sick leave, and holidays.
• Company will provide laptop and other needed computer equipment.