Head of Sales- North America (f/m/d)

Awin•Chicago, IL

5d•Hybrid

About The Position

The Head of Sales, North America defines and executes regional sales strategy, drives sustainable new-business revenue growth, and leads a high-performing Sales organisation across North America. The role owns regional sales performance, pipeline development, forecasting, and commercial execution, while staying closely involved in strategic opportunities and complex negotiations. The position develops the regional sales plan in line with company revenue objectives, global commercial priorities, and regional market opportunities. It leads and develops the Sales organisation, establishes performance and pipeline disciplines, sponsors priority prospects, and builds senior relationships with advertisers, agencies, strategic partners, and other stakeholders. The Head of Sales also collaborates with cross-functional and global teams, shares market intelligence, represents the company at industry and client events, and provides senior leadership with data-led updates on performance, opportunities, risks, resources, and investment priorities. The role requires extensive sales experience, including sales-team leadership, ownership of significant new-business targets, and experience with strategic or enterprise opportunities. Advanced CRM proficiency, sales analytics and forecasting capabilities, strong English, and willingness to travel across North America and internationally are also specified. Awin offers a hybrid working model, a four-day Flexi-Week at full pay without reducing annual holiday allowance, a monthly work-expense contribution and home-office furniture package, insurance coverage, retirement contributions, paid time off, special leaves, wellbeing initiatives, learning and development, and peer-to-peer recognition. The stated compensation range is $290,000–$350,000 OTE.

Requirements

At least 10 years of experience in Sales, Business Development, affiliate or partnership marketing, digital marketing, ecommerce, SaaS, MarTech, AdTech, or another technology-led B2B environment.
At least 5 years of experience leading Sales teams and/or Sales leaders within a complex commercial organisation.
Proven success owning and delivering significant new-business revenue targets and regional go-to-market strategies.
Demonstrated experience leading complex enterprise or strategic opportunities involving senior decision-makers.
Strong knowledge of pipeline management, forecasting, conversion, pricing, and negotiation.
Commercial leadership and sound judgement, balancing near-term delivery with sustainable growth.
Strategic thinking and the ability to translate company priorities into clear regional plans.
Credible, hands-on sales leadership and the ability to coach others through complex opportunities.
Strong people leadership, executive presence, and stakeholder influence.
Analytical, data-led decision-making and disciplined performance management.
Collaborative and adaptable approach in an international, fast-moving environment.
Advanced proficiency with Salesforce or a comparable CRM platform.
Strong capability with sales analytics, pipeline reporting, and forecasting tools.
Proficiency with Microsoft 365 and modern sales intelligence and productivity tools.
Excellent written and verbal English.
Willingness to travel across North America and internationally as required.

Nice To Haves

Experience in affiliate, partnership, or performance marketing is highly advantageous.
Professional qualifications or executive education in sales leadership, negotiation, coaching, digital marketing, or business leadership are advantageous but not essential.

Responsibilities

Define and execute the North America sales strategy in alignment with company revenue objectives, global commercial priorities, and regional market opportunities.
Develop the annual regional sales plan, setting priorities across target segments, verticals, and strategic opportunities.
Own North America new-business revenue targets, pipeline performance, forecasting, and commercial outcomes.
Lead, develop, and inspire a high-performing regional Sales organisation, fostering accountability, collaboration, coaching, and continuous improvement.
Set performance expectations and build leadership capability and succession strength across the Sales function.
Ensure adequate pipeline coverage, opportunity quality, and progression through rigorous CRM, forecasting, and deal-review disciplines.
Monitor pipeline creation, conversion, win rate, sales cycle, deal quality, and revenue delivery, using insights to improve performance and resource allocation.
Act as executive sponsor for priority prospects and strategic opportunities, supporting executive-level discovery, presentations, commercial negotiations, and complex deal progression.
Build senior relationships with advertisers, agencies, strategic partners, and other key North American stakeholders.
Partner with Marketing, Client Services, Product, Finance, and global Sales leadership on go-to-market coordination and client handovers.
Translate client, competitor, and market intelligence into recommendations to strengthen commercial positioning, propositions, and routes to market.
Represent the company at relevant industry conferences, client engagements, and commercial events across North America.
Provide senior leadership with data-led updates on regional performance, opportunities, risks, resource requirements, and investment priorities.

Benefits

Four-day Flexi-Week at full pay, with one lighter or completely disconnected day per week and no reduction to annual holiday allowance.
Hybrid working model.
Monthly work-expense contribution.
Furniture package to support a home workspace.
Comprehensive health, vision, and dental coverage, plus life insurance protection for the employee and family. Health, dental, and vision premiums are 100% covered for the employee and 50% for eligible spouses; coverage eligibility begins on the first of the month after hire.
Regular employer contributions to support long-term retirement savings through a 401(k).
Competitive personal time off and sick days.
Paid special leaves, including maternity and paternity leave.
Health and wellbeing initiatives.
Learning and development via Awin Academy.
Peer-to-peer recognition programmes.