Head of Sales

Anchorbase is a venture-backed fintech and automation company building a modern merchant operations and payments platform for businesses across North America.

We combine payment processing, intelligent workflow automation, and AI-enabled operational tooling to help merchants simplify payments, improve reconciliation, reduce operational friction, and modernize how they interact with their financial systems.

Anchorbase is an AI-centric company. We believe modern operators should use the best available tools to move faster, think more clearly, reduce manual work, improve decision-making, and create better customer and team experiences. We expect leaders at Anchorbase to personally adopt AI-enabled tools and help their teams use them intelligently across daily workflows.

Unlike traditional payment processors, Anchorbase focuses heavily on operational excellence, implementation quality, support quality, and long-term merchant success. We believe the way we sell, onboard, support, and grow merchant relationships should feel as thoughtful and professional as the platform itself.

Our team consists of experienced operators, founders, and builders who move quickly, think deeply about execution, experiment often, and care obsessively about delivering exceptional experiences for our customers.

We are currently in an early high-growth phase, backed by venture capital partners from Silicon Valley and Atlanta’s fintech ecosystem, with strong early momentum and significant long-term opportunity ahead.

Anchorbase is hiring a Head of Sales to build and scale a best-in-class BDR team while managing and growing our Account Executive function.

This is not a traditional sales management role.

This is a foundational go-to-market leadership role responsible for building the front-end revenue engine that helps Anchorbase transition from founder-led sales to a scalable, repeatable go-to-market motion.

You will own pipeline generation across the BDR team and partner-sourced channels. You will recruit and develop early-career sales professionals, establish the sales development infrastructure, and create the operating cadence required to consistently generate qualified product demonstration meetings.

We want our Account Executives to feel like Anchorbase gives them the tools, coaching, customer insight, and operating discipline required to win the right customers, create trust quickly, and build durable merchant relationships.

This role requires a leader who is deeply comfortable with experimentation and modern AI-enabled selling platforms. You will be expected to personally use and evaluate tools that improve sourcing, research, prospecting, messaging, call preparation, coaching, follow-up, CRM hygiene, reporting, and performance management. You will also be responsible for enabling your team to use these tools in ways that improve efficiency, quality, and outcomes.

You will report directly to the CEO and work closely with the founding team to help define the GTM operating system, sales development motion, partner management systems, performance expectations, hiring standards, coaching systems, and cultural habits that shape how Anchorbase scales.

This role is for someone who understands how to build both people and systems. The right leader will not only help BDRs and Account Executives hit targets, but will help create the structure, discipline, professionalism, experimentation mindset, and activity-to-outcome accountability required for a scalable revenue organization.

Build and scale a best-in-class sales development organization and Account Executive program

The BDR team should feel focused, energized, accountable, well-coached, AI-enabled, and proud of the work they are doing.

The Account Executive program should feel organized, professional, clearly managed, commercially productive, and easy for strong partners to engage with.

We want BDRs to feel like they are part of a serious, high-performance environment where they are being challenged, supported, developed, and prepared for long-term success.

We want Account Executives to operate with strong customer conviction, disciplined pipeline ownership, and a clear focus on helping merchants solve real operational problems through Anchorbase’s platform.

We want Anchorbase to become known for building one of the strongest early-career sales environments and partner ecosystems in fintech.

Attain or exceed sales development and partner-sourced pipeline targets while architecting and building a best-in-class BDR team, Account Executive program, GTM operating cadence, and performance culture.

• Build, manage, and scale the BDR function at Anchorbase.

• Build the front-end revenue engine for Anchorbase through outbound, referral, and partner-sourced motions.

• Lead the hiring process for BDR classes of approximately 5–7 people every 90–120 days.

• Design and manage 30, 60, and 90-day onboarding and ramp plans for BDRs.

• Improve time-to-productivity for new BDR hires.

• Coach and train early-career sales professionals into high-performing BDRs.

• Establish a high-performance sales development culture rooted in accountability, urgency, preparation, experimentation, and continuous improvement.

• Ensure the BDR team consistently generates qualified product demonstration meetings.

• Own BDR team performance against activity, pipeline, meeting, and conversion targets.

• Create clear visibility into leading indicators, lagging indicators, conversion rates, and pipeline quality.

• Conduct regular call reviews, coaching sessions, performance reviews, and team training.

• Establish a management operating rhythm around coaching, call review, pipeline inspection, performance improvement, and team development.

• Maintain strong CRM hygiene and source attribution across HubSpot and related sales systems.

• Use funnel data, activity data, call quality, and conversion metrics to guide coaching and decision-making.

• Build repeatable systems for interviewing, onboarding, training, performance management, and career development.

• Develop the BDR organization into a talent bench for future account executive and sales leadership roles.

• Evaluate, implement, and personally use AI-enabled selling tools that improve sourcing, prospecting, research, messaging, outreach, call preparation, coaching, follow-up, reporting, and CRM hygiene.

• Train the BDR/Account Executive team to use AI-enabled selling platforms responsibly and effectively to improve productivity, personalization, prioritization, and sales execution.

• Experiment with new tools, workflows, prompts, data sources, and automation systems that improve sales development productivity and quality.

• Oversee the Account Executive function, including partner sourcing, onboarding, activation, enablement, communication, accountability, and performance management.

• Build systems and standards for how Account Executives are recruited, trained, activated, supported, and measured.

• Ensure Account Executives understand Anchorbase’s platform, ideal customer profile, positioning, sales process, and referral expectations.

• Manage ongoing partner relationships with professionalism, responsiveness, and commercial discipline.

• Track partner-sourced opportunities, conversion rates, activity levels, and revenue contribution.

• Identify high-performing partners and help them grow their contribution to Anchorbase.

• Help create the culture, standards, tooling expectations, and operating cadence that define Anchorbase’s go-to-market organization.
  

We are looking for a metric-driven sales leader, team builder, partner operator, and AI-forward builder.

The ideal candidate likely has:

• 8+ years of experience in sales development, business development, partnerships, channel sales, or go-to-market leadership.

• 5+ years of leadership experience in an outbound sales organization.

• Experience managing at least 5 direct reports.

• Demonstrated success hiring, training, and developing early-career sales professionals.

• Proven experience scaling a BDR or SDR team, ideally up to 20+ people within an 18-month period.
  

• Proficiency with CRM for funnel management, lead management, partner tracking, reporting, source attribution, and data quality.

• Strong sales training skills, especially for professionals early in their careers.

• Demonstrated curiosity and practical experience using AI-enabled tools to improve sourcing, research, outreach, coaching, reporting, and team productivity.

• Comfort experimenting with new workflows, automation, AI tools, sales platforms, and data-driven performance systems.
  

You do not need to come from fintech or payments, though that experience is valuable.

You do need to be highly structured, highly accountable, deeply people-oriented, commercially sharp, AI-curious, and capable of building serious sales development and partner management systems from the ground up.

Anchorbase is a startup environment built by experienced founders and operators.

We move quickly, communicate directly, and care deeply about execution quality.

We are AI-centric in how we think, build, sell, operate, and scale. We expect leaders to be hands-on users of modern tools, not passive observers of the changing technology landscape. Leaders at Anchorbase should actively experiment, teach their teams what works, abandon what does not, and continuously improve how work gets done.

We are looking for people who take ownership, think critically, solve problems proactively, communicate professionally, and genuinely care about team and partner outcomes.

This role is not designed for someone looking for a fully mature sales organization, rigid corporate infrastructure, legacy sales management habits, or a passive management role.

This role is for builders.

You will be expected to lead from the front, create structure where it does not yet exist, hold a high bar, personally adopt modern selling tools, and help shape the habits, systems, and culture of two important go-to-market functions.

• Location: Toronto, Canada

• Reports to: CEO

• Function: Sales / Partnerships

• Salary + performance bonus structure

• Significant long-term growth opportunity

• Direct exposure to founding team

• Opportunity to help shape a rapidly growing venture-backed fintech company
  

Compensation will be commensurate with experience, leadership capability, and demonstrated ability to build high-performing teams and partner programs.

Most sales leadership roles inherit an existing machine.

This role is about building the environment, systems, tools, and operating cadence that create high performance across both internal sales development and external partner channels.

Anchorbase is at the stage where the systems, habits, expectations, technology choices, and culture created by this leader will have an outsized impact on the company’s trajectory.

You will have the opportunity to work directly with the CEO, build a BDR team from the ground floor, develop early-career professionals, shape the outbound motion, manage Account Executives, implement AI-enabled selling workflows, and help create one of the most important engines of Anchorbase’s growth.

This is an opportunity to help build something meaningful from the ground floor.