co-founder & ceo - ai benefits & insuretech

co-founder & ceo - ai for aec project proposals

co-founder & ceo - ai for credit and finance

2026-2027 yearlong quality inspections intern

avp, financial planning & analysis Jobs in Person Jobs In Person Jobs In Person Jobs In Chicago

avp, financial planning & analysis

co-founder & ceo - ai benefits & insuretech Jobs in Person Jobs In Person Jobs In Person Jobs In Chicago

co-founder & ceo - ai for aec project proposals Jobs in Person Jobs In Person Jobs In Person Jobs In Chicago

co-founder & ceo - ai for credit and finance Jobs in Person Jobs In Person Jobs In Person Jobs In Chicago

co-founder & ceo - ai ria compliance Jobs in Person Jobs In Person Jobs In Person Jobs In Chicago

co-founder & ceo - ai ria compliance

co founder ceo ai for credit and finance

FutureSight

<div>FutureSight is seeking an experienced and visionary Founding CEO to lead the launch of a new AI-native loan covenant monitoring and compliance platform for mid-market borrowers.
CFOs and controllers are stuck managing covenant compliance through brittle spreadsheets and manual reporting, translating real-time ERP data into rigid bank formats under constant risk of technical default. At the same time, banks and credit funds waste enormous analyst time chasing data and validating calculations instead of managing risk.
We&rsquo;re building a borrower-first compliance layer that sits between accounting systems and loan agreements. The platform automatically translates ERP data into lender-specific covenant logic, generates bank-ready compliance certificates, and surfaces early breach risk &mdash; without changing bank systems.
This is an opportunity to build a category-defining AI platform in a $2B+ market, redefining how mid-market borrowers manage credit compliance.
As Founding CEO, you will<ul><li>
Win customers &mdash; Run pilots, shape pricing, and validate retention + expansion.</li><li>
Build the product &mdash; Work with FutureSight&rsquo;s product/engineering pod to launch V1.</li><li>
Raise capital &mdash; Lead the seed round with our initial investment.</li><li>
Build your team &mdash; Hire your founding team and set the cultural foundation.</li></ul>
About FutureSight
FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage &mdash; pairing hands-on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x.
We&rsquo;re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
What We Bring<ul><li>
Validated problem &mdash; You will enter a venture with a proven market need and strong momentum toward building and scaling.</li><li>
Studio bench strength &mdash; Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.</li><li>
Capital commitment &mdash; Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network.</li></ul>
What You Bring<ul><li>
Founder-level drive &mdash; You&rsquo;re motivated to co-found a new venture as the CEO. With or without us, this is your calling.</li><li>
Startup scrappiness &mdash; You know what you&rsquo;re signing up for. You&rsquo;re familiar with the scrappiness of owning something from start to finish.</li><li>
Previous founding experience &mdash; You have co-founded a product company or B2B SaaS venture, or have been at a venture-backed company.</li><li>
Risk appetite and capacity &mdash; Read more on our post on the Entrepreneurial Risk Profile.</li><li>
GTM chops &mdash; Proven success in B2B SaaS sales, marketing, and customer engagement.</li><li>
Fundraising fluency &mdash; Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities.</li><li>
People leadership &mdash; Magnet for top talent; coach and culture carrier.</li><li>
Industry experience &mdash; Experience in lending, credit, finance, or CFO B2B SaaS, with hands-on exposure to financial reporting, compliance workflows, or risk management.</li></ul>
What You Can Expect<ul><li>
Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise.</li><li>
Full P/L ownership of the new entity.</li><li>
A significant equity stake in the business.</li><li>
This is a full-time role; we are seeking someone to dedicate themselves full-time and exclusively to building and owning a new SaaS venture.</li></ul>
Ready to build? 
If this is the perfect opportunity for you, we want to hear from you!
Submit your Resume and LinkedIn profile and tell us more about why you think we should chat!
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.</div>

Co-Founder & CEO - AI for Credit and Finance

<div>FutureSight is seeking an experienced and visionary Founding CEO to lead the launch of a new AI data infrastructure venture serving the $20B+ employee benefits ecosystem across brokers, MGAs, and mid-market employers.
Today, brokers and HR teams struggle to make data-driven decisions because benefits data is often locked in carrier portals, PDFs, and spreadsheets, leading to opaque renewals, manual reporting, and poor cost control.
Our venture is building an AI-powered data platform that automatically extracts and standardizes benefits data from carriers and brokers, producing instant renewal models, benchmarking insights, and compliance-ready dashboards. The result: faster renewals, clearer cost transparency, and smarter plan design.
As Founding CEO, you will<ul><li>
Win customers &mdash; Run pilots, shape pricing, and validate retention + expansion.</li><li>
Build the product &mdash; Work with FutureSight&rsquo;s product/engineering pod to launch V1.</li><li>
Raise capital &mdash; Lead the seed round with our initial investment.</li><li>
Build your team &mdash; Hire your founding team and set the cultural foundation.</li></ul>
About FutureSight
FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage &mdash; pairing hands-on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x.
We&rsquo;re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
What We Bring<ul><li>
Validated problem &mdash; You will enter a venture with a proven market need and strong momentum toward building and scaling.</li><li>
Studio bench strength &mdash; Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.</li><li>
Capital commitment &mdash; Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network.</li></ul>
What You Bring<ul><li>
Founder-level drive &mdash; You&rsquo;re motivated to co-found a new venture as the CEO. With or without us, this is your calling.</li><li>
Startup scrappiness &mdash; You know what you&rsquo;re signing up for. You&rsquo;re familiar with the scrappiness of owning something from start to finish.</li><li>
Previous founding experience &mdash; You have co-founded a product company or B2B SaaS venture or have been at a venture-backed company.</li><li>
Risk appetite and capacity &mdash; Read more on our post on the Entrepreneurial Risk Profile.</li><li>
GTM chops &mdash; Proven success in B2B SaaS sales, marketing, and customer engagement.</li><li>
Fundraising fluency &mdash; Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities.</li><li>
People leadership &mdash; Magnet for top talent; coach and culture carrier.</li><li>
Industry experience &mdash; Background in employee benefits, brokerage, or insurtech / HR data products.</li></ul>
What You Can Expect<ul><li>
Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise.</li><li>
Full P/L ownership of the new entity.</li><li>
A significant equity stake in the business.</li><li>
This is a full-time role; we are looking for someone to commit full-time and exclusively to building and owning a new SaaS venture.</li></ul>
Ready to build? 
If this is the perfect opportunity for you, we want to hear from you!
Submit your Resume and LinkedIn profile and tell us more about why you think we should chat!
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.</div>

Co-Founder & CEO - AI Benefits & InsureTech

<div>FutureSight is seeking an experienced, visionary Founding CEO to lead the launch of a new AI Sales platform explicitly designed for wholesale distributor sales reps. 
Industrial wholesale distributors serving the HVAC, electrical, and plumbing markets face a perfect storm: experienced sales reps are retiring with decades of product knowledge, causing 6-12 months of productivity loss per retirement, while manual quoting can take hours to days when speed determines who wins deals. Distributors turn down 80% of RFPs due to capacity constraints, struggling to manage 100,000+ SKU catalogues and hire staff fast enough. This $2B TAM is growing at 25-30% annually with no dominant player. 
 
The solution is an AI assistant that serves the complete distributor sales workflow, including inside sales, outside sales, commercial quoting, and counter sales. It transforms hours into seconds through real-time quote generation, automates RFQ processing with ERP integration, processes contractor takeoffs into accurate quotes, provides point-of-sale AI for counter staff, captures institutional expertise in the system, and delivers real-time cross-sell intelligence as a unified all-in-one platform for the complete front-office sales workflow.
As Founding CEO, you will<ul><li>
Win customers &mdash; Run pilots, shape pricing, and validate retention + expansion.</li><li>
Build the product &mdash; Work with FutureSight&rsquo;s product/engineering pod to launch V1</li><li>
Raise capital &mdash; Lead the seed round with our initial investment</li><li>
Build your team &mdash; Hire your founding team and set the cultural foundation</li></ul>
About FutureSight
FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage &mdash; pairing hands-on studio support with early capital, reducing risk and increasing the odds of success by 10x.
We&rsquo;re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise; Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time-exited founder; and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
What We Bring<ul><li>
Validated problem &mdash; You will enter a venture with a proven market need and strong momentum toward building and scaling.</li><li>
Studio bench strength &mdash; Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1</li><li>
Capital commitment &mdash; Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network</li></ul>
What You Bring<ul><li>
Founder-level drive &mdash; You&rsquo;re motivated to co-found a new venture as the CEO. With or without us, this is your calling.</li><li>
Startup scrappiness &mdash; You know what you&rsquo;re signing up for. You&rsquo;re familiar with the scrappiness of owning something from start to finish.</li><li>
Previous founding experience &mdash; You have co-founded a product company or B2B SaaS venture or have been at a venture-backed company.</li><li>
Risk appetite and capacity &mdash; Read more on our post on the Entrepreneurial Risk Profile</li><li>
GTM chops &mdash; Proven success in B2B SaaS sales, marketing, and customer engagement</li><li>
Fundraising fluency &mdash; Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities.</li><li>
People leadership &mdash; Magnet for top talent; coach and culture carrier</li><li>
Industry experience &mdash; Background in building integrated sales SaaS products, working in parallel with ERPs.</li></ul>
What You Can Expect<ul><li>
Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise</li><li>
Full P/L ownership of the new entity</li><li>
A significant equity stake in the business</li><li>
This is a full-time role; we are seeking someone to dedicate themselves full-time and exclusively to building and owning a new SaaS venture.</li></ul></div>

Co-Founder & CEO - AI Sales for Wholesale Distributors

<div>FutureSight is hiring an experienced and visionary Founding CEO to lead the launch of a new AI Compliance venture serving SEC- and FINRA-regulated firms. Today, compliance teams at RIAs and broker-dealers spend countless hours manually reviewing marketing materials, employee communications, and trade records&mdash;driving up costs, slowing approvals, and increasing exam risk.
Our venture is reimagining this workflow with an explainable, policy-as-code platform that brings all reviews into one intelligent, automated system&mdash;empowering compliance teams to move faster, cut costs, and stay confidently audit-ready.
As Founding CEO, you&rsquo;ll shape the vision, build the team, and lead this transformation across the $10B regulatory technology market.
As Founding CEO, you will<ul><li>
Win customers &mdash; Run pilots, shape pricing, and validate retention + expansion</li><li>
Build the product &mdash; Work with FutureSight&rsquo;s product/engineering pod to launch V1
</li><li>Raise capital &mdash; Lead the seed round with our initial investment</li><li>
Build your team &mdash; Hire your founding team and set the cultural foundation</li></ul>
About FutureSight
FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage &mdash; pairing hands-on studio support with early capital, reducing risk and increasing the odds of success by 10x.
We&rsquo;re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
What We Bring<ul><li>
Validated problem &mdash; You will enter a venture with a proven market need and strong momentum toward building and scaling</li><li>
Studio bench strength &mdash; Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1</li><li>
Capital commitment &mdash; Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network</li></ul>
What You Bring<ul><li>
Founder-level drive &mdash; You&rsquo;re motivated to co-found a new venture as the CEO. With or without us, this is your calling.</li><li>
Startup scrappiness &mdash; You know what you&rsquo;re signing up for. You&rsquo;re familiar with the scrappiness of owning something from start to finish</li><li>
Previous founding experience &mdash; You have co-founded a product company or B2B SaaS venture or have been at a venture-backed company</li><li>
Risk appetite and capacity &mdash; Read more on our post on the Entrepreneurial Risk Profile</li><li>
GTM chops &mdash; Proven success in B2B SaaS sales, marketing, and customer engagement</li><li>
Fundraising fluency &mdash; Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities</li><li>
People leadership &mdash; Magnet for top talent; coach and culture carrier</li><li>
Industry experience &mdash; Background in financial compliance, wealth management, or RegTech (SEC/FINRA familiarity strongly preferred).</li></ul>
What You Can Expect<ul><li>
Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise</li><li>
Full P/L ownership of the new entity</li><li>
A significant equity stake in the business</li><li>
This is a full-time role; we are looking for someone to commit full-time and exclusively to building and owning a new SaaS venture</li></ul>
Ready to build? 
If this is the perfect opportunity for you, we want to hear from you!
Submit your Resume and LinkedIn profile and tell us more about why you think we should chat!
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.</div>

Co-Founder & CEO - AI RIA Compliance

<div>FutureSight is seeking an experienced, visionary Founding CEO to lead the launch of a new AI-native platform that transforms how architecture, engineering, and construction (AEC) firms win project pursuits and proposals.
AEC firms are drowning in complexity. Proposal and marketing teams juggle chasing technical experts, searching through outdated project experience and content, and manually tracking requirements across RFQs, RFPs, and qualification packages &mdash; coordinating across business development, technical leaders, and executives under tight deadlines.
The result: slower submissions, inconsistent win rates, and significant operational strain in a process directly tied to firm growth and backlog visibility.
We&rsquo;re building BidOps &ndash; an AI-native proposal platform for AEC firms that automates requirement and compliance tracking, intelligently reuses institutional knowledge and proposal content, and streamlines coordination across technical experts.
Firms move faster, reduce submission risk, and pursue more opportunities with the same teams.
As Founding CEO, you will<ul><li>
Win customers &mdash; Run pilots, shape pricing, and validate retention + expansion.</li><li>
Build the product &mdash; Work with FutureSight&rsquo;s product/engineering pod to launch V1.</li><li>
Raise capital &mdash; Lead the seed round with our initial investment.</li><li>
Build your team &mdash; Hire your founding team and set the cultural foundation.</li></ul>
About FutureSight
FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage &mdash; pairing hands-on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x.
We&rsquo;re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
What We Bring<ul><li>
Validated problem &mdash; You will enter a venture with a proven market need and strong momentum toward building and scaling.</li><li>
Studio bench strength &mdash; Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.</li><li>
Capital commitment &mdash; Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network.</li></ul>
What You Bring<ul><li>
Founder-level drive &mdash; You&rsquo;re motivated to co-found a new venture as the CEO. With or without us, this is your calling.</li><li>
Startup scrappiness &mdash; You know what you&rsquo;re signing up for. You&rsquo;re familiar with the scrappiness of owning something from start to finish.</li><li>
Previous founding experience &mdash; You have co-founded a product company or B2B SaaS venture, or have been at a venture-backed company.</li><li>
Risk appetite and capacity &mdash; Read more on our post on the Entrepreneurial Risk Profile.</li><li>
GTM chops &mdash; Proven success in B2B SaaS sales, marketing, and customer engagement.</li><li>
Fundraising fluency &mdash; Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities.</li><li>
People leadership &mdash; Magnet for top talent; coach and culture carrier.</li><li>
Industry experience &mdash; Background in government contracting, proposal management, or B2B SaaS for professional services.</li></ul>
What You Can Expect<ul><li>
Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise.</li><li>
Full P/L ownership of the new entity.</li><li>
A significant equity stake in the business.</li><li>
This is a full-time role; we are seeking someone to dedicate themselves full-time and exclusively to building and owning a new SaaS venture.</li></ul>
Ready to build? 
If this is the perfect opportunity for you, we want to hear from you!
Submit your Resume and LinkedIn profile and tell us more about why you think we should chat!
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.</div>

Co-Founder & CEO - AI for AEC Project Proposals

Alignerr

<div>
 
 About The Role
 
 
 
 We&rsquo;re looking for entrepreneurship instructors to help evaluate AI systems trained on startups, innovation, and business planning.
 
 
 <ul>
 <li>
 Organization: Alignerr (Powered by Labelbox)
 </li>
 <li>
 Location: Remote
 </li>
 <li>
 Type: Hourly / Task-based Contract
 </li>
 <li>
 Compensation: $35-70 /hour
 </li>
 <li>
 Commitment: 10-40 hours/week
 
 
 </li>
 </ul>
 
 What You&rsquo;ll Do
 
 
 
 <ul>
 <li>
 Review startup and entrepreneurship scenarios used in AI training.
 </li>
 <li>
 Assess business models, assumptions, and go-to-market logic.
 </li>
 <li>
 Identify unrealistic projections or flawed reasoning.
 </li>
 <li>
 Provide structured feedback to improve practical relevance.
 </li>
 <li>
 Work independently and asynchronously to meet project deadlines.
 
 
 </li>
 </ul>
 
 Who You Are
 
 
 
 <ul>
 <li>
 3+ years of experience teaching entrepreneurship or small business.
 </li>
 <li>
 Strong understanding of business models and early-stage decision-making.
 </li>
 <li>
 Able to critically evaluate written business plans and scenarios.
 </li>
 <li>
 Comfortable providing applied, real-world feedback.
 
 
 </li>
 </ul>
 
 Nice to Have
 
 
 
 <ul>
 <li>
 MBA or entrepreneurship-focused graduate degree.
 </li>
 <li>
 Founder or startup advisory experience.
 </li>
 <li>
 Familiarity with AI or content evaluation workflows.
 
 
 </li>
 </ul>
 
 Why Join Us
 
 
 
 <ul>
 <li>
 Competitive pay and flexible remote work.
 </li>
 <li>
 Lead a team working on cutting-edge AI projects.
 </li>
 <li>
 Exposure to advanced LLMs and how they&rsquo;re trained.
 </li>
 <li>
 Freelance perks: autonomy, flexibility, and global collaboration.
 </li>
 <li>
 Potential for contract extension.
 
 
 </li>
 </ul>
 
 Application Process (Takes 10-15 min)
 
 
 
 <ul>
 <li>
 Submit your resume
 </li>
 <li>
 Complete a short screening
 </li>
 <li>
 Project matching and onboarding
 
 
 </li>
 </ul>
 
 PS: Our team reviews applications daily. Please complete your AI interview and application steps to be considered for this opportunity.
 
</div>

Entrepreneurship Instructor (AI Training)

zesty.ai

<div><h1 class="jobSectionHeader">Controller</h1>

Location: Remote (US) 
Reports to: Chief Financial Officer
<h2 class="jobSectionHeader">
About ZestyAI</h2>

ZestyAI is the leading property and climate risk analytics platform for the P&amp;C insurance industry. Our AI-powered models provide property-level insights into the risks that drive the majority of losses, including wildfire, hail, and water damage. Using proprietary data from aerial imagery, property characteristics, permits, and environmental signals, we help insurers price accurately, underwrite smarter, and reduce losses &ndash; creating a stronger and more resilient insurance market. As climate events grow more frequent and complex, legacy models can no longer keep pace. ZestyAI replaces outdated assumptions with dynamic, property-specific intelligence. Our next wave of innovation leverages agentic and generative AI to accelerate decision-making across the insurance value chain.
<h2 class="jobSectionHeader">
The Opportunity</h2>

We are hiring a Controller to build and lead a modern, automation-first accounting function at a rapidly growing AI company.

This is a rare opportunity to design the financial control environment of an AI-native platform company from the ground up.

We are intentionally building a flat, highly capable finance team where senior leaders operate as high-impact individual contributors and leverage automation, outsourced partners, and AI agents to maximize efficiency. You will work directly with the CFO to:
<ul>
<li>Professionalize accounting policies and monthly close process</li>
<li>Design scalable accounting processes and infrastructure</li>
<li>Implement scale-appropriate financial controls</li>
<li>Drive automation across close, reporting, and compliance</li>
<li>Build a finance function that scales to $100M+ without unnecessary headcount</li>
</ul>
If you are a technically strong Controller who is curious, self-directed, and already experimenting with AI in your current finance workflows, this role puts you at the forefront of how AI reshapes accounting. You will not be constrained by legacy systems or bureaucracy. You will be empowered to build.
<h1 class="jobSectionHeader">
What You'll Do</h1>
<h2 class="jobSectionHeader">Own the Accounting Function</h2>
<ul><li>Lead the monthly, quarterly, and annual multi-entity close process; produce accurate consolidated GAAP financial statements (P&amp;L, Balance Sheet, Cash Flow)</li>
<li>Managing outsourced bookkeeping</li>
<li>Develop accounting policies, SOPs, and internal controls</li>
<li>Manage/oversee AP, AR, payroll accounting, reconciliations</li>
<li>Maintain reconciliations, schedules, and documentation at audit-ready standards</li>
</ul><h2 class="jobSectionHeader">Revenue &amp; Contract Accounting</h2>
<ul><li>Own revenue recognition policy and execution (including complex data licensing and multi-element contracts)</li>
<li>Partner with Go-To-Market and Legal to ensure contract structures align with accounting treatment</li>
<li>Maintain deferred revenue schedules and ensure billing, collections, and reporting are clean and reconciled</li>
</ul><h2 class="jobSectionHeader">Controls, Risk &amp; Audit</h2>
<ul><li>Design and implement scalable internal controls</li>
<li>Prepare the company for financial audits and future diligence</li>
<li>Partner cross-functionally to ensure control maturity aligns with growth</li>
<li>Build documentation and workflows that support compliance and enterprise customer requirements</li>
</ul><h2 class="jobSectionHeader">Automation &amp; AI-Driven Finance</h2>
<ul><li>Lead the accounting systems roadmap (ERP, close tools, bill pay, spend management)</li>
<li>Leverage automation to reduce manual journal entries and reconciliation work</li>
<li>Identify and implement AI agents or workflows to assist with:</li>
<li><ul><li>Reconciliations</li>
<li>Contract review</li>
<li>Close checklists</li>
<li>Policy drafting</li>
<li>Variance analysis</li>
</ul></li><li>Establish an &quot;automation-first&quot; mindset across the finance function</li>
</ul>
You will have wide latitude to test, implement, and scale AI tooling inside finance.
<h2 class="jobSectionHeader">
Vendor &amp; Outsourced Partner Oversight</h2>
<ul><li>Manage outsourced bookkeeping, tax, payroll, and other accounting support</li>
<li>Establish clear service standards and quality expectations</li>
<li>Ensure outsourced workflows integrate seamlessly with internal systems</li>
</ul><h2 class="jobSectionHeader">Cash &amp; Financial Discipline</h2>
<ul><li>Oversee AP/AR workflows and improve billing and collections rigor</li>
<li>Strengthen working capital management</li>
<li>Support cash forecasting accuracy through clean accounting data</li>
</ul><h1 class="jobSectionHeader">What We're Looking For</h1>
<ul><li>7+ years of progressive accounting experience</li>
<li>Strong US GAAP foundation including CPA and audit experience (either auditor-side or company-side)</li>
<li>Experience in high growth recurring revenue software startup</li>
<li>Experience managing revenue with enterprise contracts</li>
<li>Familiarity with enterprise sales commission plans</li>
<li>Proven experience operating in a lean or growth-stage environment</li>
<li>Experience managing audits and building documentation discipline</li>
<li>Demonstrated ability to improve processes and implement systems</li>
</ul><h2 class="jobSectionHeader">Bonus Points For</h2>
<ul><li>Experience in Insurtech, fintech, data platforms, or AI-driven companies</li>
<li>ERP implementation experience</li>
<li>Hands-on experimentation with AI tools in accounting workflows</li>
<li>Clear examples of automation initiatives you have personally driven</li>
</ul><h1 class="jobSectionHeader">Who You Are</h1>
<ul><li>Curious and self-directed</li>
<li>Comfortable building in ambiguity</li>
<li>Energized by improving systems rather than maintaining legacy processes</li>
<li>Highly accountable and detail-oriented</li>
<li>Excited by AI's role in reshaping finance operations</li>
<li>Motivated by impact and ownership, not title hierarchy</li>
</ul>
You've likely already found ways to use AI in reconciliations, policy writing, close management, or analysis &mdash; and you're eager to go further.
<h1 class="jobSectionHeader">
Why Join ZestyAI</h1>
<ul><li>Join a recognized AI and Insurtech leader reshaping risk analytics</li>
<li>Work directly with executive leadership in a high-impact role</li>
<li>Build a modern accounting function designed for scale</li>
<li>Operate in a flat team with significant ownership</li>
<li>Be at the forefront of AI adoption in finance operations</li>
</ul>
This is a career-defining opportunity for a Controller who wants to build &mdash; not just maintain.</div>

Controller (Remote)

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