Head of Sales (вакансія неактивна)

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.