Account Executive

Description

Flexi Software is seeking a driven and relationship focused Account Executive to own new business development within the insurance and financial services markets. This role is a hybrid working environment and in-office time is 2-3 days per week. This is a high impact, high ownership role for a seller who thrives in complex, consultative deal cycles and wants to work at a company where winning deals actually matters. You will carry a focused book of named accounts, manage a full sales cycle and work closely with solutions, marketing, and executive leadership to build a repeatable pipeline in a market Flexi is purpose built to serve.

About Flexi

Flexi Software has been a trusted provider of accounting solutions for over 30 years, offering cloud based and on-premise software tailored for organizations with complex accounting requirements. We serve insurance carriers, banks, credit unions, and financial services firms. Flexi is known for its depth of functionality, multi-entity architecture, and the kind of customer support that creates long term clients.

Roles and Responsibilities

• Own a named territory where you will build and manage a pipeline of qualified opportunities from first contact through closed-won
• Execute a disciplined, multi-touch prospecting motion across cold outreach, referrals, industry events, and inbound lead follow-up
• Lead discovery conversations with CFOs, Controllers, and finance operations leaders to uncover accounting pain, business fit, and competitive landscape
• Partner with the solutions team to design and deliver compelling, customer-specific product demonstrations
• Manage deal progression through a structured sales process (MEDDPICC or equivalent); maintain accurate and up-to-date Salesforce hygiene throughout
• Drive contract and pricing negotiations through close, working with legal and leadership on MSAs and SOWs as needed
• Collaborate with marketing on campaign feedback, content needs, and event strategy for the insurance vertical
• Represent Flexi at industry conferences
• Provide accurate monthly and quarterly pipeline forecasting to sales leadership

Requirements

• 3+ years of full‑cycle B2B software sales experience, with a consistent record of quota attainment
• Experience selling into finance or accounting buyers (CFO, Controller, VP Finance) required
• Background in ERP, accounting software, or financial technology strongly preferred; insurance industry experience is a significant plus
• Demonstrated ability to manage 3 to 6 month deal cycles with multiple stakeholders and technical evaluation components
• Proficiency in Salesforce CRM; disciplined in pipeline management and forecasting
• Strong discovery and qualification skills; comfortable holding the room in executive level conversations
• Ability to self source pipeline through prospecting, networking, and referrals, not just inbound lead follow‑up
• Familiarity with MEDDPICC or a comparable structured sales methodology is a plus

Personal Characteristics

• High ownership mentality: you treat your territory like a business and take personal accountability for results
• Relentlessly curious about your buyers; you do the research, understand the pain, and come to every meeting prepared
• Competitive and motivated by winning, but collaborative and low‑ego with teammates and internal partners
• Comfortable operating with ambiguity in a growing company where process is still being built, not handed to you
• Organized and methodical: you know what is in your pipeline, where each deal stands, and what the next step is
• Genuine interest in the insurance and financial services market; you want to become a subject matter expert, not just a quota carrier
• Positive communicator who builds trust with buyers and internal stakeholders alike
• Positive attitude and sense of humor; we work hard and like the people we work with

Flexi provides excellent benefits including paid holidays and paid time off, a 401(k) plan with company participation, health and dental insurance, life and disability insurance, and a vision discount plan.

Only candidates under consideration will be contacted. Any offer of employment will be contingent upon a positive criminal background check.

No phone calls, please. Principals only.

Drug‑free workplace. M/F/V/H EEO