Remote Insurance Software Sales Jobs in Santa Rosa, CA

Account Executive

Hybrid- Field and office Full-Time Reports to Regional Sales Manager

About AIO

AIO is building the AI-native operating system for the restaurant industry - purpose-built software and hardware that replaces the fragmented, legacy systems operators have been forced to manage for decades. We move fast, operate lean, and hold ourselves to a high standard.

The Role

As an Account Executive at AIO, you own a territory from first conversation to closed deal - and you stay close to your customers through installation and onboarding to make sure they actually get value. This is a full-cycle sales role: you source, qualify, demo, negotiate, close, and hand off well. SDRs will feed you qualified appointments, but you are expected to generate pipeline independently and carry your own outbound activity alongside the inbound flow.

The restaurant operators you will sell to are busy, skeptical of technology vendors, and have been burned before. Your job is to earn their trust quickly, understand their actual operational challenges, and show them how AIO solves problems they deal with every day. This is consultative selling, but it requires conviction and urgency. AIO is a fast-moving company in a market ready to be disrupted, and the AE who wins here combines genuine curiosity about the customer with a relentless drive to close.

Core Responsibilities

Territory Ownership & Pipeline Generation

• Own an assigned geographic territory - know your market, know your accounts, and build a systematic plan to cover it

• Generate pipeline independently through outbound prospecting: calls, in-person visits to restaurant locations, and targeted outreach to owners and decision-makers

• Work closely with your assigned SDRs to maximise qualified appointment flow - provide clear feedback on lead quality and help sharpen targeting

• Maintain a pipeline at 3x quota coverage at all times; flag gaps early and close them through your own activity

Discovery & Qualification

• Run thorough discovery calls to understand each operator's current tech stack, operational pain points, decision-making process, and timeline

• Qualify rigorously - not every restaurant is the right customer today, and time spent on poor-fit deals is time not spent on winnable ones

• Build a clear picture of the buying committee: who influences, who decides, who needs to be in the room for the demo

• Use BANT, MEDDIC, or equivalent qualification frameworks consistently and log findings in HubSpot before moving stages

Product Demos & Proposal

• Deliver tailored product demos that connect AIO features directly to the specific pain points uncovered in discovery - no generic walkthroughs

• Handle objections with confidence and honesty; if something is not right for the customer today, say so and revisit when timing changes

• Build and present commercial proposals clearly; understand your own deal economics and be comfortable discussing ROI with operators

• Run A/B testing on demo formats and messaging - what resonates with QSR operators may land differently with fine dining - and share what you learn

Pipeline Management & Closing

• Move deals through the pipeline with discipline - each stage should have clear exit criteria and a defined next step before you leave the conversation

• Forecast your pipeline accurately and honestly.

• Communicate pipeline status and deal risk to your RSM weekly - no surprises at end of quarter

• Close with urgency and without desperation; operators respond to confidence, clarity, and a compelling reason to move now

• Keep HubSpot current at every stage - deal notes, contact records, next steps, and close dates must reflect reality, not optimism

Customer Handoff & Onboarding Partnership

• Own the transition from closed deal to live customer - you introduced AIO, you set the expectations, you are responsible for making sure the handoff to the Field Operations and Installation team is clean

• Stay engaged through installation and initial onboarding; customers who feel abandoned after signing churn faster and refer less

• Surface early customer feedback to the product and customer operations teams - you are closest to the customer in the first 90 days

• Build relationships that generate referrals; a restaurant operator who loves AIO knows twenty others who should

Market Intelligence & Cross-Functional Contribution

• Provide structured feedback to Marketing on what messaging lands, what objections recur, and what competitive intelligence you are picking up in the field

• Stay current on restaurant industry trends, competitor offerings, and the operational challenges facing operators in your territory

• Participate actively in team meetings, sales training, and pipeline reviews - your market knowledge makes the whole team sharper

What We're Looking For

• 24 years of B2B SaaS sales experience with a track record of quota attainment - restaurant tech, hospitality technology, or SMB-focused SaaS is a strong advantage

• Full-cycle sales experience: you have sourced, run discovery, demoed, negotiated, and closed - not just one part of the funnel

• Genuine comfort with outbound prospecting; you do not wait for the phone to ring, and you are not afraid to walk into a restaurant and introduce yourself

• Strong discovery and consultative selling instincts - you ask better questions than you give answers, and you listen to what the customer is actually saying

• HubSpot proficiency is required - you will live in it daily for contact management, deal tracking, sequences, activity logging, and pipeline reporting. Sloppy CRM hygiene is a performance issue here, not an administrative one

• Ability to run compelling, customized demos without leaning on a script.

• Clear, direct communicator - with customers, with SDRs, and with internal stakeholders

• High adaptability in a fast-moving startup environment; the playbook is still being written, and you will help write it

• Familiarity with Sandle, BANT, MEDDIC, SPIN, Challenger, or equivalent qualification and sales frameworks

Nice to Have

• Prior experience working in a restaurant - as a server, manager, operator, or any front- or back-of-house role. If you have lived the problem we are solving, you will build trust with operators faster than anyone

• Experience selling directly to restaurant owners, GMs, or multi-unit operators - you know how they think, what they distrust, and what actually moves them

• Familiarity with restaurant POS systems, kitchen display systems, or hospitality tech platforms

• Background in high-velocity, short-cycle SaaS sales where activity and urgency drive results

What This Is Not

This is not an order-taking role. AIO does not have a large brand presence that opens doors: you open doors. If you are looking for a well-worn enterprise sales process with full SDR coverage, a large marketing team, and a mature brand, this is not the right fit. If you want to own your territory, build something real, and be rewarded for what you close, you will thrive here.

Why AIO

• Own your territory and your outcomes: your compensation is directly tied to what you close. Top performers earn disproportionately here.

• Real product-market fit in a market ready for disruption: the $55B restaurant tech market is still dominated by legacy systems. You are selling a genuinely better solution.

• Short sales cycles: restaurant operators make decisions quickly. You see the results of your work and your paycheck without waiting quarters.

• SDR support: qualified appointments land on your calendar so you can focus your selling energy on deals that matter.

• A company that values your market intelligence: what you learn in the field shapes how we build, market, and sell. Your voice is heard here.

• Values that mean something: Accountability, Love the Grind, and Reach Further Together are how this team operates not how it presents itself.