Job 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 positive criminal background check. No phone calls, please. Principals Only. Drug-free workplace. M/F/V/H EEO

Requirements

Must-haves

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.
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
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
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
Only candidates under consideration will be contacted. Any offer of employment will be contingent upon positive criminal background check.
No phone calls, please. Principals Only.
Drug-free workplace. M/F/V/H EEO

Nice-to-haves

Background in ERP, accounting software, or financial technology strongly preferred; insurance industry experience is a significant plus
Familiarity with MEDDPICC or a comparable structured sales methodology is a plus

Application prep

Use the role’s language and application details while tailoring your materials.

Platform: paylocity
Effort: medium

Benefits

Benefits detected in the listing.

Dental

Vision

401(K)

Paid Time Off