Role Overview

The Head of Sales & Customer Success owns the full commercial lifecycle — from first outbound touch to long-term retention — with a decisive bias toward new revenue generation. You are, first and foremost, a Hunter: you will personally run inbound demos, architect outbound systems, and coach a small team to close mid-market and enterprise deals with urgency. Secondarily, you are the Defender of the existing base: you oversee Customer Success and Support to protect NRR, neutralize churn, and drive expansion. This is a player-coach seat. You manage a lean, multi-functional team (BDR, AE, Account Manager, Support) and are expected to be in the deal, not just above it.

Key Responsibilities

• Outbound engine & pipeline architecture - Primary focus Architect and own the "cold-to-closed" outbound system: sequence design, BDR workflow, SQL volume targets, and continuous A/B iteration. Deploy AI-driven workflows for lead research, hyper-personalized outreach at scale, and meeting transcript analysis — eliminating low-leverage manual prospecting tasks for the BDR team. Personally run high-stakes discovery calls and demos, demonstrating elite objection handling and value-based closing techniques to the team in real time. Design and maintain the full sales playbook: outreach cadences, email templates, objection-handling wikis, and closing scripts that encode your best instincts into repeatable systems.
• Inbound funnel mastery - Primary focus Own end-to-end conversion for organic and paid inbound leads: speed-to-lead, qualification, demo scheduling, and close. Maintain a demo show rate above 85% through automated AI-reminders and tight pre-demo qualification. Identify and eliminate friction at every stage of the mid-to-bottom funnel to compress sales cycle length.
• Sales team leadership & coaching - Primary focus Directly manage BDRs and AEs using an LMA (Leadership, Management, Accountability) framework in a remote-first, high-accountability culture. Coach the team on discovery, demo delivery, advanced objection handling, and closing — turning reps into commercial operators, not order-takers. Run structured forecast reviews and pipeline hygiene sessions; zero tolerance for "dark funnel" activity outside HubSpot.
• HubSpot ownership & revenue forecasting Architect the CRM deal stages to accurately reflect the buyer's journey for both inbound and outbound channels. Maintain 100% data integrity for lead attribution, deal forecasting, and pipeline velocity — HubSpot is the single source of truth, no shadow systems. Deliver weekly, monthly, and quarterly revenue forecasts grounded in historical conversion rates and pipeline data.
• Customer success & retention - Supporting function Oversee Account Managers and Support Specialists, transitioning the team from reactive ticket-handling to a proactive revenue-defense model. Segment the customer portfolio by spend velocity, industry, and risk profile; deploy tiered engagement playbooks (white-glove for high-velocity agencies; automated touchpoints for SMBs). Proactively identify at-risk accounts through usage signals and health metrics before cancellation requests surface — deploy "save" playbooks early. Drive expansion and upsell revenue within the existing base to sustain NRR above 105%. Ensure 100% of high-velocity and agency accounts receive a verified ROI report (money saved / CAC reduced) at regular intervals.

Mandatory requirements

• 7+ years in senior Sales, CS, or Account Management roles within B2B SaaS — with clear ownership of New Business (CAC), Churn, and Expansion (NRR).
• 5+ years of hands-on experience building and scaling outbound sales systems, including multi-channel sequence design and BDR management against aggressive SQL targets.
• Proven track record as a direct closer: running live demos and navigating complex objections through to "Closed Won" on mid-market or enterprise deals.
• Expert-level HubSpot proficiency: lifecycle management, automation, deal-stage architecture, and reporting.
• Analytically self-sufficient: comfortable performing deep-dive analysis on traffic patterns, churn signals, and conversion bottlenecks without relying on a dedicated Data analyst.
• Demonstrated AI implementation: architected and deployed autonomous agents or multi-step automations (LLM APIs, Make.com, custom GPTs) that eliminated at least 50% of manual overhead in a sales or support function.
• Multi-functional remote leadership: proven success managing BDRs, AEs, and CSMs in a high-accountability, distributed environment.

Nice to have

• Deep PPC / ad fraud domain knowledge: Google Ads (MCC), Meta, Bing, and sophisticated IVT pattern recognition.
• Fluency in the language of Media Buyers and CMOs — selling "ROAS protection" and "budget efficiency," not just software features.
• Experience selling or supporting "black box" autonomous tech where value must be consistently unpacked through data reporting.
• Prior work within or for a performance marketing agency; familiarity with agency churn dynamics and "silent defense" client retention needs.
• Advanced outbound intelligence stack experience: Apollo.io, Clay, Instantly.ai integrated into HubSpot for automated prospecting engines.
• Advanced prompt engineering or custom GPT-building applied to specific CS or sales bottlenecks.
• EOS familiarity: comfortable operating within the Integrator/Visionary dynamic, owning departmental Rocks, and leading Level 10 meetings.

About Us

ClickGUARD is a SaaS startup operating in a domain where ad tech meets cybersecurity (you should consider subscribing to our YouTube channel to find out more about us). Our platform helps Google Ads advertisers protect their investment and maximize their ROI by detecting and removing wasteful ad traffic from their advertising campaigns. We’ve built the absolute best solution for a significant problem for PPC advertisers, and we need your help taking it to the next level of user experience.

How we work

We're a fully remote company with a close-knit team that’s figured out how to onboard employees the right way and build an awesome team spirit even when spread out across the globe. So come take a look and maybe join us.