Reply.io, a leading sales engagement platform, empowers Sales Development Representatives (SDRs) with AI-driven tools to discover leads, engage across multiple channels, and scale outbound sales effectively. We are now looking for a Head of Sales to join our team and help drive the next stage of our growth. PURPOSE: Why does this job exist? This role exists to lead Reply.io’s sales transformation and growth, scaling our new AI product Jason AI from early traction to a sustainable revenue engine. The Head of Sales will drive the journey to double current ARR by the end of 2026, building a world-class sales team capable of supporting Reply’s global expansion and long-term vision. ACCOUNTABILITIES: What are the key deliverables? The Head of Sales will contribute to Reply.io’s success through: * Revenue growth: Drive significant year-on-year growth of Jason AI, establishing it as the core contributor to company revenues. * Pipeline health: Build and maintain predictable pipeline coverage (≥3x quota) across all AE tiers. * Sales team building: Hire, coach, and grow a 10–15 AE organization across SMB+, Mid-Market segments. * Go-to-market excellence: Execute a diversified AE model by product, geography, ICP, and vertical. * Sales process optimization: Implement the SPICED methodology, improve S2 conversion rates and enforce pipeline discipline. * Enablement & culture: Create a competitive, growth-driven sales culture where the best talent earns the best opportunities. * Collaboration: Partner with Marketing, Product, and CS to ensure alignment of GTM execution with corporate strategy
ACTIVITIES: What does the jobholder have to do? Leadership of the Sales Team * Act as the face of sales internally and externally, representing sales in the management team. * Lead, coach, and mentor AEs, building clear career progression paths (from junior → senior). * Transform juniors into A-players while keeping personal involvement in closing high-value deals.
Organization of Sales Team * Implement a 5-dimensional AE structure (level, product, segment, geography, ICP) * Own recruitment, incentive plans, and comp structures. * Set revenue targets and ensure fair pipeline distribution across team tiers. * Balance focuses on Jason AI growth in MM segment while supporting legacy Sales Engagement products.
Sales Gearbox / Ways of Working * Lead weekly pipeline reviews and implement disciplined 1:1 coaching practices. * Standardize demo flows, talk tracks, and qualification frameworks (SPICED). * Introduce AI-driven enablement tools for routing, qualification, and automation. * Ensure alignment with CEO/RevOps/Marketing/CS for sales process planning and execution.
Reporting and Forecasting * Own visibility into the sales funnel, pipeline, and forecast accuracy. * Track and report on SaaS metrics such as: * MRR growth & New Business ACV * Win rates & stage-to-stage conversion rates * Quota attainment % per AE * Pipeline coverage (3—4x quota) * Sales cycle length & CAC payback * Drive a data-driven discipline in Hubspot and sales reporting practices.
Major Client Work * Lead from the front: sell deals directly to stay relevant in the field. * Own strategic account management in the SMB/MM segments. * Act as gatekeeper for pricing, terms, and strategic deal approvals, balancing growth with profitability.
RELATIONSHIPS: Who does the jobholder have to work with? * CEO and leadership team — for strategic alignment. * Customers & partners — as a trusted advisor and deal closer. * Sales team — AEs across SMB, and MM. * Internal colleagues — especially Marketing, CS, Product, and RevOps to ensure GTM alignment.
REQUIREMENTS * 5+ years of sales experience in the B2B and Software/SaaS idustry. * Proven track record of scaling ARR through SMB and Mid-Market segments. * Experience hiring, coaching, and managing AE teams is a plus. * Expertise in building predictable pipelines, structuring comp plans, and driving quota attainment. * Hands-on knowledge of sales methodologies. * Data-driven mindset with excellent command of SaaS metrics. * Strategic thinker with strong execution skills — able to balance building processes with closing deals. * Excellent communication and leadership skills, comfortable representing sales internally and externally. * Experience selling AI, productivity, or SaaS products to global SMB/MM markets is a plus.
WHAT WE OFFER * A long-term role with ownership and real impact on Reply.io’s global sales strategy. * Opportunity to scale a new AI product (Jason AI) into a market-leading revenue engine. * Remote-first work with flexible hours and optional co-working coverage. * A supportive, no-micromanagement culture with strong leadership backing. * 15 paid vacation days, national holidays & ~10 days of Christmas vacation. * Sick leaves without limitations. * Access to internal training, knowledge sessions, and professional development resources. * A friendly and ambitious team, working on a product loved by customers worldwide.
