Director of Sales

Anchor closed $40M in top-tier VC funding and grew 500% last year, transforming the $74B services payments market. We're hiring an AI-First Director of Sales to own new logo revenue and build a modern, AI-First sales org from scratch.

This isn’t a role where AI is a nice-to-have. It’s the operating system. Every process you touch - outbound, pipeline review, forecasting, enablement, hiring - will be rebuilt as AI-first. You’ll architect a sales engine where AI agents, automation, and intelligent tooling eliminate manual work at every stage of the pipeline. You’ll hire a lean, high-leverage team of SDRs, BDRs, and AEs who operate as force multipliers alongside AI, delivering 3x the output of a traditional org with a fraction of the headcount.

Reporting to the COO. Player-coach. Entrepreneurial mindset. AI hands-on experience. Deeply tech savvy - you build, configure, and adopt tools yourself, you don’t wait for someone else to set them up. High-energy. Fast-paced. Hungry to grow.

The AI-First Mandate

Anchor is building an AI-first organization from the ground up. This isn’t a transformation project - it’s how we operate by default. As Director of Sales, you will be expected to drive exponential value by turning every sales process into an AI-first workflow: eliminating manual, repetitive work; replacing human effort with AI agents wherever possible; and enabling each member of your team to deliver exponential output. 

You will be accountable for continuously auditing your function and eliminating work that AI can own - from prospecting research to pipeline updates, from call summaries to forecast rollups. If a human is doing it and AI can do it better or faster, you build the system. The speed of AI adoption and the measurable productivity leverage per rep are core performance metrics in this role.

• Own new logo revenue end-to-end: outbound pipeline creation, inbound conversion, and close.
• Build an AI-First sales org from scratch. Hire, train, and manage a team that uses AI agents, co-pilots, and automation as core workflow, not bolt-on tools.
• Architect AI-powered outbound where AI handles research, personalization, and signal detection. Your BDRs orchestrate, not manually send emails.
• Lead strategic deals personally while coaching reps through full-cycle execution with AI-assisted call analysis, deal scoring, and competitive intel.
• Maximize inbound with AI-driven scoring, routing, and speed-to-lead. No gut feel.
• Build predictive operations using AI-driven forecasting, pipeline analytics, and CRM automation so reps spend time selling, not on admin.
• Create dynamic enablement with playbooks, battlecards, and prospecting frameworks kept current and personalized through AI.
• Innovate the GTM model continuously. Experiment on segmentation, messaging, and AI-assisted tactics. Measure. Iterate. Scale what works.
• Collaborate cross-functionally with Marketing, CS, Product, and Dev to align execution and feed AI models with cross-functional data.

• AI-first mindset with receipts. You're already using AI to drive exponential impact. You can name the tools you've implemented, the workflows you've automated, and the productivity gains you've measured. Real results, not just familiarity.
• 8+ years in B2B SaaS sales (SMB/Mid-Market), including 3+ years leading a team of 5+ reps. Consistent quota attainment and ARR growth in high-growth environments. A promotion within your sales leadership track is a strong plus.
• Sales org builder with a proven track record of standing up SDR, BDR, and AE functions from scratch.
• Full revenue ownership in end-to-end new logo responsibility in outbound-driven environments.
• AI & sales tech fluency with practical experience across AI tools, conversation intelligence, intent data, predictive analytics, and CRM automation.
• Player-coach who leads deals and develops people simultaneously.
• Executive presence. Confident C-level communicator who can articulate technical, contractual, and financial value.
• Data-driven operator who makes decisions with pipeline data and AI insights, not intuition.
• Startup grit. Thrives in ambiguity, moves fast, builds structure as you go.

• Background in fintech, payments, or financial services SaaS.
• Experience selling into accounting firms, bookkeeping firms, or CFO organizations.
• Bachelor's degree or MBA in accounting/finance.