Vice President of Software Sales

Oscar is working with a leading B2B provider of cash solutions organization that is looking for an experienced VP of Software Sales to join their team.

We are seeking a Vice President of Software Sales to lead revenue growth across North America. This role is responsible for driving end-to-end enterprise sales, expanding our presence within retail banks and large retailers, and building long-term strategic relationships with key stakeholders.

Key Responsibilities:

Own the full sales lifecycle across North America, including pipeline development, qualification, solution selling, negotiation, and deal closure for SES AI Forecasting.
Develop and execute a targeted territory strategy focused on Tier 1 and Tier 2 retail banks and large-scale retailers with complex cash operations.
Build and maintain a strong sales pipeline through direct outreach, partnerships, industry events, and referrals, with a target contribution of $3M-$5M+ ARR within 24 months.
Lead executive-level discovery sessions and value-based workshops with senior stakeholders, including CFOs, Heads of Treasury/Cash, and Retail Operations leaders.
Partner with Pre-Sales and Product teams to deliver tailored demonstrations and develop compelling, data-driven business cases aligned to client needs.
Represent at industry events and establish a strong market presence within the banking and retail ecosystem.
Provide market insights and customer feedback to inform product strategy and go-to-market initiatives.
Maintain accurate forecasting and pipeline reporting within CRM systems.

Required Qualifications:

10+ years of experience in enterprise B2B sales or business development within SaaS, FinTech, or banking technology.
Proven success closing complex, multi-stakeholder SaaS deals with financial institutions or large retailers.
Strong understanding of retail banking operations, cash management, treasury, or supply chain processes.
Established network within North American banking or retail sectors.
Demonstrated ability to build and present executive-level business cases and ROI models.

Skills and Competencies:

Expertise in strategic account planning and consultative, value-based selling.
Strong commercial acumen, including structuring and negotiating enterprise SaaS agreements.
Exceptional communication skills with strong executive presence and C-suite engagement experience.
Highly self-motivated and able to operate independently in a fast-paced, scale-up environment.
Fluent in English; Spanish or Portuguese is a plus.

Preferred Qualifications:

Experience with cash management technologies, ATM networks, cash-in-transit services, or forecasting platforms.
Familiarity with AI/ML-based forecasting or supply chain optimization solutions.
Background working with or at organizations such as Glory, Diebold Nixdorf, Loomis, Brink's, or similar providers.
Experience in U.S. and Canadian financial services markets.
Bachelor's degree in Business, Finance, or Technology; MBA preferred.

Recap:

Location: Fully Remote

Type: Permanent Fulltime

Salary: 190k-200k base salary + Benefits

If you think you're a good fit for the role, we'd love to hear from you!

Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.