About This Role

Title: Director of Sales

Reports to: CRO

Location: Remote (East/Central US)

Employment Type: Full-time

About Bettermode

Bettermode is a fast-growing B2B SaaS platform that helps mid-market and enterprise companies build modern customer communities that drive engagement, advocacy, and retention. Backed by investors such as CRV and Bessemer, we’re scaling from $5M ARR toward $20M+ with a small, high-impact team of 30+.

We’re hiring a Director of Sales to help scale Bettermode’s sales motion. You will carry a full quota, run deals end-to-end, and help raise the bar across the team through coaching, deal support, and consistent execution as we grow.

The Opportunity

This is a quota-carrying, hands-on sales role for a proven closer who can also lead by example. You will run deals end-to-end, build pipeline, and help raise the bar across the team through coaching, deal support, and sharing what works.

This role reports directly to the CRO and will work tightly with Marketing, Product, and Customer Experience to improve win rates, shorten cycles, and turn strong product momentum into repeatable revenue.

What You’ll Do

Close Deals and Own a Full Quota

• Own a full quota and a defined territory/segment
• Run the full sales cycle: discovery, demo, evaluation, negotiation, and close
• Build and execute a deal strategy for every active opportunity (mutual plans, next steps, multi-threading)
• Navigate procurement and legal in partnership with the CRO and internal teams

Build Pipeline (Not Just Work Inbound)

• Consistently generate pipeline through outbound and account planning
• Work closely with SDR support (if applicable) and help improve outbound messaging and targeting
• Partner with Marketing on campaign follow-up, conversion quality, and feedback loops

Lead by Example (Team Lead, Not People Manager)

• Coach peers through deal support, call reviews, and sharing what works
• Help improve team execution: discovery quality, objection handling, and close discipline
• Bring a high bar for CRM hygiene, follow-up, and operating cadence

Forecasting and Sales Operating Rhythm

• Maintain clean pipeline, clear next steps, and accurate stage progression in CRM
• Support weekly pipeline reviews and forecast calls with the CRO
• Improve win rates, conversion, and sales cycle time through better qualification and process

Cross-Functional Leadership

• Bring customer and market signal back to Product: objections, feature gaps, competitor intel
• Coordinate with Customer Experience on handoffs and early customer outcomes
• Partner with Marketing on positioning feedback and proof points that move deals forward

What You Bring

• 6 to 10+ years of B2B SaaS closing experience, with a consistent track record of hitting quota
• Experience in a startup or high-growth environment where you had to build pipeline and figure things out
• Strong discovery and deal leadership across complex buying groups (marketing leaders and cross-functional stakeholders)
• Comfortable with outbound, account planning, and multi-threading
• Strong operating discipline: CRM hygiene, follow-up, next steps, and forecasting
• A natural coach who helps the team win through examples, deal support, and direct feedback
• Experience selling mid-market and low-enterprise SaaS is a plus

Cultural Values

We’re looking for someone who lives our core values:

• 🎯 Focus: Eliminate noise, drive meaningful results.
• ⚡️ Bold: Take smart risks and challenge the status quo.
• ⛰️ Grit: Stay resilient through challenges and push through discomfort.
• 🤝 Accountability: Take ownership, deliver, and support your teammates.
• 🚀 Ambition: Set audacious goals and pursue them relentlessly.

Benefits

🌟 At Bettermode, we’re dedicated to empowering our team to thrive both professionally and personally. We offer location-based, competitive compensation that reflects your expertise and impact, with annual reviews so you can grow with us. Our culture is built on ownership and trust, giving you real influence over how we scale and succeed.

🩺 From your very first day, you and your family are covered by comprehensive Canadian health benefits—dental and vision included—so you can focus on what matters most.

😎 Enjoy unlimited paid vacation days, paid parental leave to support your family, and bereavement leave should you need it.

🛠️ You’ll have all the equipment you need provided, or you can bring your own device and access our Device Upgrade Policy—an interest-free hardware stipend repayable via payroll deductions, allowing you to upgrade when you need.

💡 We want you to thrive in your work: every team member receives a monthly Tech & Appreciation Stipend—perfect for testing new tools and improving your workflows as you see fit.