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

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