Head of Sales

Reporting to:
CEO

Location:
Italy / Milan (with international travel)

Work model:
On-site at Milan HQ with the option of
1 day per week remote working

Seniority:
5–10 years preferred

About UpSurgeOn

UpSurgeOn is a fast-growing MedTech company pioneering surgical simulation and performance-based training. Starting from hyper-realistic physical simulators, UpSurgeOn is evolving into a new growth phase (2026–2030) focused on AI-powered coaching, data-driven skill assessment, and scalable digital training experiences. By combining simulation, performance analytics and certification pathways, the company aims to enable surgical excellence globally and unlock new value for MedTech companies, hospitals and insurance ecosystems.

Role overview

UpSurgeOn is looking for a
Head of Sales
to build and lead a structured, scalable commercial engine during a key growth phase.

This is a
hands-on leadership role
, designed for someone who combines
strong execution and strategic capability
: a leader able to close complex B2B deals, build a repeatable sales machine, coach a commercial team, and create a scalable go-to-market structure across regions, channels and products (physical + digital).

The ideal candidate has:

• proven ability to drive
  high-value B2B sales cycles
  , with executive stakeholders and long-cycle negotiations
• discipline in forecasting, pipeline management and sales operations
• leadership capacity to mentor and elevate team performance
• strong recruiting ability to build and scale the team over time
• strategic marketing mindset to shape positioning and demand generation
• deep familiarity with the
  surgical ecosystem
  , with proven experience selling into surgical markets and stakeholders (MedTech, hospitals, training institutions)
• a track record in complex B2B sales beyond healthcare
  (enterprise, industrial, SaaS, training platforms, or other high-value B2B environments), with measurable results and strong deal economics discipline

The mission
is to grow revenue and margins, ensure predictable sales performance, strengthen strategic partnerships, and build a sales organization capable of scaling globally.

What you will own

1) Revenue growth & pipeline execution

• Own revenue targets across key segments (MedTech, hospitals, training institutions, insurance ecosystems and strategic partners).
• Drive end-to-end sales execution: prospecting, qualification, needs discovery, proposal, negotiation, closing and handover.
• Build a reliable pipeline engine across regions and strategic accounts.
• Ensure strong conversion rates, deal momentum, and consistent quarterly performance.
• Establish execution cadence: pipeline reviews, deal desk, win/loss analysis, and action-driven follow-ups.

2) Strategic account development, partnerships & channel network

• Develop and grow relationships with top MedTech customers, strategic accounts and partners.
• Build multi-geography expansion strategies within existing customers (same product → more geographies; more products → same customer; full portfolio → global).
• Support and coordinate key distribution partnerships (e.g.,
  Artimedica in Mexico
  or other channel/distribution models).
• Build, manage and optimize a network of distributors, agents and local commercial partners, including onboarding, governance, incentives, and performance monitoring.
• Create long-term customer value and recurring revenue opportunities (bundles, renewals, digital subscriptions).

3) Sales strategy, segmentation & GTM execution

• Translate company strategy into a clear commercial plan: target segments, value proposition, pricing logic, channel strategy and country prioritization.
• Define territories, account assignment rules and coverage model.
• Set clear objectives and performance targets for each salesperson and partner.
• Shape product positioning and commercial packaging for physical and digital offerings.
• Partner with Product/R&D to align roadmap and commercial priorities based on market signals and customer needs.

4) Marketing-oriented leadership & demand generation strategy

• Work closely with Marketing to define strategic demand generation priorities and campaign logic.
• Contribute to positioning and messaging, ensuring that value proposition is clear and aligned with the decision-making dynamics of the surgical market.
• Activate KOL networks, events, and strategic channels to increase pipeline quality and brand credibility.
• Strengthen commercial narrative: pitch decks, messaging frameworks, use cases, and competitor differentiation.

5) Deal economics, pricing & margin discipline

• Ensure each deal is evaluated through profitability and margin impact (gross margin, delivery costs, payment terms).
• Strengthen pricing structure and discount governance (rules, approval flows, decision logic).
• Support the CEO in high-stakes negotiations and strategic deal decisions.
• Improve commercial discipline around contract terms, payment schedules, and risk reduction.

6) Sales operations, forecasting & reporting

• Build and maintain a structured CRM discipline and reporting cadence.
• Own forecasting accuracy and rhythm: monthly/quarterly forecasting, pipeline reviews, risk flags.
• Define and monitor KPIs: pipeline coverage, cycle time, conversion rates, average deal size, win/loss reasons, churn/renewals (if applicable).
• Provide CEO and leadership with clear synthesis: what is happening, why, and what decisions/actions to take.

7) Team mentoring, recruiting & performance culture

• Lead, mentor and coach the existing sales team, raising capabilities and performance standards.
• Build the sales org over time through recruiting, onboarding, training, performance management.
• Create sales playbooks: pitch structure, objections, negotiation, expansion strategy, account planning.
• Establish a strong results-driven culture based on accountability, ownership and execution excellence.

8) Cross-functional execution

• Work tightly with Operations / Production to align delivery feasibility, lead times, and customer expectations.
• Collaborate with Finance to ensure healthy sales-to-cash execution (collections discipline, payment terms, revenue predictability).
• Coordinate with the CEO and leadership team to align priorities and commercial strategy.
• Serve as internal reference for customer intelligence and market signals.

Required qualifications

• Degree in Business, Economics, Engineering, or equivalent.
• 5–10+ years of relevant sales experience
  , combining:
• complex B2B sales (high-ticket, multi-stakeholder, long cycle)
• hands-on closing ability + structured sales leadership
• proven track record in
  structured B2B markets beyond healthcare
  (enterprise / industrial / SaaS / services), with measurable results
• Proven ability to sell to senior decision-makers (C-level, directors, procurement, clinical leaders).
• Strong negotiation and contract management skills.
• Strong analytical discipline: pipeline, forecasting, deal economics, CRM rigor.
• Strong communication skills with non-sales stakeholders; ability to influence without authority.
• High reliability, ownership mindset, and execution discipline.
• Fluent in Italian and English (written and spoken).

Preferred qualifications

• Experience in MedTech, medical devices, surgical ecosystem or training environments.
• Experience selling hybrid offerings: physical products + digital solutions / SaaS / subscriptions.
• International sales exposure and multi-region account expansion.
• Experience building sales teams and processes in scale-ups.
• Experience managing distributors / resellers / agents and channel governance.
• Strong CRM proficiency (Odoo, HubSpot, Salesforce or similar).

Core competencies

• Strategic thinking + execution rigor
• Strong closing mindset and deal discipline
• Results orientation and accountability culture
• Sales forecasting precision and operational excellence
• Stakeholder management at executive level
• Ability to build systems from scratch in ambiguity
• High energy, resilience and leadership presence

Success metrics (first 6–12 months)

• Clear sales strategy and segmentation implemented (accounts, territories, channel model, pipeline structure).
• Measurable improvement in:
• pipeline coverage and conversion
• forecasting accuracy
• gross margin discipline per deal
• sales cycle efficiency
• Commercial cadence adopted (weekly pipeline review, monthly forecast, KPI dashboard).
• Key strategic accounts expanded across geographies and product portfolio.
• Channel and partner network structured with clear governance and measurable performance.
• Repeatable playbooks and sales process documented and used by the team.
• Strong mentoring impact: clear improvement in team execution and accountability.

Compensation & Growth

Base salary:
to be defined based on seniority and fit — benchmark range typically
€55k RAL + up to €30k variable
.

Bonus:
performance-based variable linked to revenue, margin and strategic milestones.

Growth path:
this is a
CRO-track role
, with progressive expansion to full revenue responsibility as the company scales.