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Описание: |
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.
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