Sales Executive-SaaS Solutions

Success Systems is seeking a high-performing, full-cycle SaaS Account Executive to drive new customer acquisition and expansion revenue for our cloud-based retail software solutions. The Account Executive will own opportunities from outbound prospecting and qualification through discovery, product demonstration, business-case development, commercial negotiation, and closed-won handoff.

This role is ideal for a consultative seller who can help retail and convenience-store operators modernize their business through software that improves visibility, execution, profitability, compliance, reporting, inventory management, promotions, labor efficiency, and multi-location control.

The successful candidate is highly accountable, comfortable creating pipeline from scratch, skilled at engaging senior business leaders, and disciplined in managing a structured sales process. This is a quota-carrying position with responsibility for both new-logo business and growth within assigned accounts or territories.

Key Responsibilities

• Own the end-to-end sales process for Success Systems SaaS solutions, including prospecting, qualification, discovery, demonstration, proposal development, negotiation, closing, and post-sale handoff.
• Generate new business through outbound prospecting, targeted account outreach, inbound lead follow-up, referrals, partner relationships, industry events, and account-based selling.
• Build relationships with retail owners, executives, operations leaders, finance leaders, IT stakeholders, merchandising teams, and other decision-makers.
• Conduct discovery to understand customer goals, business processes, technology environment, reporting needs, operational inefficiencies, compliance requirements, and growth priorities.
• Position Success Systems software as a business solution rather than a feature set, linking product capabilities to measurable operational, financial, and strategic outcomes.
• Deliver tailored demonstrations and executive presentations that align to each prospect’s use cases and decision criteria.
• Develop compelling ROI analyses, value hypotheses, mutual action plans, proposals, and commercial packages.
• Manage multiple opportunities simultaneously while maintaining a strong, predictable pipeline.
• Create and execute territory and account plans that identify high-value target accounts, expansion opportunities, key stakeholders, and competitive displacement strategies.
• Work closely with sales development, marketing, customer success, implementation, product, and leadership teams to accelerate revenue growth and improve customer outcomes.
• Navigate procurement, security, legal, finance, and executive approval processes as necessary.
• Maintain accurate CRM records, including contacts, account plans, discovery notes, opportunity stages, next steps, deal risks, close dates, forecasts, and competitive intelligence.
• Meet or exceed assigned targets for annual recurring revenue, bookings, new-logo acquisition, pipeline creation, conversion rates, and expansion revenue.
• Monitor industry trends, customer needs, competitor positioning, and product-market opportunities in convenience-store and retail technology.

Required Qualifications

• 3 years of full-cycle B2B SaaS sales experience with demonstrated quota attainment.
• Proven ability to source pipeline independently through outbound prospecting and strategic account development.
• Experience selling to mid-market, multi-location, enterprise, or operationally complex organizations.
• Strong consultative selling skills, including discovery, stakeholder mapping, value articulation, product demonstration, negotiation, and closing.
• Track record of managing opportunities involving multiple decision-makers and longer or more complex sales cycles.
• Ability to translate software capabilities into financial and operational business outcomes.
• Strong written and verbal communication skills, including executive-level presentation skills.
• Experience using CRM and sales-engagement tools to manage activity, pipeline, forecasting, and account information.
• Data-driven approach to territory planning, pipeline management, conversion improvement, and forecast accuracy.
• Bachelor’s degree preferred, or equivalent relevant professional experience.

Preferred Qualifications

• Experience selling SaaS solutions into convenience stores, retail, fuel retail, hospitality, restaurants, distribution, consumer goods, or multi-location operators.
• Familiarity with retail operations, back-office systems, POS ecosystems, inventory management, tobacco rebate programs, lottery, promotions, loyalty, reporting, or store analytics.
• Experience selling operational software with measurable ROI tied to margin improvement, time savings, labor efficiency, reduction in shrink, or improved compliance.
• Knowledge of modern SaaS selling methodologies, including MEDDICC, Challenger, Command of the Message, Sandler, or similar approaches.
• Experience selling through strategic partnerships, referral networks, technology alliances, resellers, or channel relationships.
• Familiarity with SaaS commercial structures, including subscription agreements, annual recurring revenue, multi-year contracts, expansion motions, and renewal economics.

Success Measures

• Annual recurring revenue and total contract value closed
• New-logo acquisition
• Pipeline creation, coverage, and progression
• Opportunity conversion rates and sales-cycle efficiency
• Average contract value and multi-year agreement penetration
• Expansion and cross-sell revenue within assigned accounts
• Forecast accuracy and CRM data quality
• Consistent attainment of monthly, quarterly, and annual quota targets
• Quality of closed-won handoff to implementation and customer success

What Success Systems Offers

• The opportunity to sell SaaS solutions that help retailers operate smarter, improve execution, and make better business decisions.
• A high-accountability environment where sellers have meaningful ownership of territory strategy and revenue outcomes.
• Competitive base salary, uncapped commission opportunity, and performance incentives.
• Access to a team with deep industry expertise in convenience-store and retail technology.
• Career development opportunities in enterprise sales, strategic accounts, partnerships, sales leadership, and go-to-market strategy.

Optional Short Posting Version

Success Systems is hiring full-cycle Account Executives to drive new business across retail technology solutions. We are seeking consultative, quota-carrying sellers who can prospect, run discovery, demonstrate solutions, build business cases, negotiate contracts, and close business with convenience-store, fuel, tobacco, lottery, and multi-location retail operators.

We have opportunities focused on:

Role

Primary Sale

Ideal Background

Account Executive – POS & Kiosk

POS systems, self-service kiosks, hardware-enabled retail technology, integrations, and services

Retail POS, kiosks, payments, fuel technology, convenience retail, or complex operational technology

Pay: $100,000.00 - $300,000.00 per year

Benefits:

• Health insurance
• Health savings account
• Paid time off
• Tuition reimbursement

Work Location: Hybrid remote in Norwalk, CT 06851

Salary : $100,000 - $300,000