Director of Product - Platform (New York)

Come build at the intersection of AI and fintech. At Ocrolus, we’re on a mission to help lenders automate workflows with confidence—streamlining how financial institutions evaluate borrowers and enabling faster, more accurate lending decisions. Our AI workflow and analytics platform for lenders is trusted at scale, processing nearly one million credit applications every month across small business, mortgage, and consumer lending. By integrating state-of-the-art open- and closed-source AI models with our human-in-the-loop verification engine, Ocrolus captures data from financial documents with over 99% accuracy. Thanks to our advanced fraud detection and comprehensive cash flow and income analytics, our customers achieve greater efficiency in risk management, and provide expanded access to credit—ultimately creating a more inclusive financial system. Trusted by more than 400 customers—including industry leaders like Better Mortgage, Brex, Enova, Nova Credit, PayPal, Plaid, SoFi, and Square—Ocrolus stands at the forefront of AI innovation in fintech. Join us, and help redefine how the world’s most innovative lenders do business. We’re looking for a Director of Product - Platform to own the foundational layer that powers everything Ocrolus builds. This role sits at the center of the company, responsible for document intelligence infrastructure, our API and developer platform, and model orchestration. You’ll define the platform strategy that enables both business units to move faster, ship better products, and scale without reinventing the wheel. This is a high-leverage, high-visibility role for someone who thinks in systems, builds for durability, and thrives when the problem is ambiguous and cross-functional. What you’ll do: Platform Strategy & Roadmap Own the product vision and roadmap for Ocrolus’s platform layer: document intelligence/extraction infrastructure, API/developer platform, and model orchestration Define platform abstractions and capabilities that serve both SMB and Mortgage business units without creating one-off solutions Make crisp prioritization decisions across competing BU needs, balancing near-term delivery with long-term platform scalability AI/ML, Automation & Agentic Services Own end-to-end human-in-the-loop learning systems, including task design, feedback loops, and data generation to continuously improve model performance Partner with the Automation and ML teams to advance document accuracy, classification models, and extraction pipelines Drive the product strategy for model orchestration, including how we evaluate, deploy, and monitor AI/ML models in production Be a thought partner to our vertical teams (SMB and Mortgage) on developing and executing agentic services. Help identify where AI agents can automate workflows, replace manual steps, and create step-function improvements in our products Translate emerging AI capabilities (LLMs, vision models, foundation models, agentic architectures) into practical platform features that create defensible competitive advantage Stay deeply curious about what’s happening in AI/ML. Read papers, break things, form opinions. We need someone genuinely excited by the technology, not managing it from a distance API & Developer Experience Own the developer-facing surface area of Ocrolus: APIs, documentation, webhooks, and integration patterns Define the platform contract that internal teams and external customers build against Drive improvements in API reliability, latency, and developer ergonomics Cross-BU Collaboration & Stakeholder Management Navigate competing priorities across SMB and Mortgage product teams, acting as the connective tissue between vertical needs and horizontal capabilities Partner closely with operations teams to ensure platform capabilities effectively handle edge cases and real-world variability in document workflows Partner with engineering leadership to align on technical architecture, capacity allocation, and build‑vs‑buy decisions Communicate platform strategy and tradeoffs clearly to executive leadership Execution & Team Building Lead a team of platform product managers Define and drive accuracy-first quality frameworks specific to document intelligence, including measurement and continuous improvement Ship iteratively with a bias toward learning, not perfection Roll up your sleeves. Prototype with code, vibe code solutions, build quick proofs-of-concept. We value PMs who do, not just spec Define platform metrics, SLAs, and health indicators that create accountability Who we’re looking for (Skill Sets and Qualifications): Experience in product management, with years of owning platform, infrastructure, or developer‑facing products Technical/engineering background (CS, engineering degree, or equivalent hands‑on experience). You can read architecture diagrams, reason about system design, and hold your own with senior engineers Deep AI fluency and intellectual curiosity. You follow what’s happening in AI/ML because you’re genuinely interested, not because the job requires it. You have opinions about model architectures, tooling, and where the space is headed Demonstrated experience building and scaling AI/ML‑powered products or platforms in production environments Hands‑on builder mentality. You’ve prototyped solutions, written code (or vibe coded) to test ideas, and don’t wait for engineering to validate every hypothesis Track record of working at growth‑stage companies (Series B‑D, $20M‑$200M ARR) where you had to build systems, not just manage them Strong cross‑functional leadership: you’ve navigated competing stakeholder priorities and made trade‑off decisions that stuck Experience managing or mentoring other product managers Experience in fintech, lending, document processing, or financial data infrastructure Preferred Qualifications: Prior experience with document intelligence, OCR, or unstructured data extraction at scale Familiarity with ML model lifecycle management: training, evaluation, deployment, monitoring Experience building API platforms or developer tools used by external customers Background in fraud detection, identity verification, or underwriting automation Contributions to open‑source projects, published technical writing, or side projects that demonstrate genuine builder instincts The full‑time salary range for this role is around $180,000 - $220,000 variable equity benefits. Base pay offered may vary depending on job‑related knowledge, skills, experience, and market location. Disclosure as required by N.Y.C. Admin. Code §§ 8-102 and 8-107(32) of the full time salary compensation range for this role when being hired into our offices in New York City. We believe diverse perspectives drive better outcomes. We are committed to fostering an inclusive workplace where everyone has a seat at the table, regardless of race, gender, gender identity, age, disability, national origin, or any other protected characteristic. J-18808-Ljbffr

Chief Information Officer (Irvine)

Department: IT Employment Type: Full Time Location: Irvine, CA Compensation: $265,000 - $300,000 / year The Chief Information Officer will serve as the company’s chief technology leader, aligning technology strategy with the company’s business strategy. The role leads the enterprise technology organization across applications, data and analytics, infrastructure and operations, and cybersecurity, and partners with executive leadership and regional teams to position technology as a trusted business partner, build a high-performing team, and provide a secure, scalable foundation that enables leaders to focus on winning work, executing projects, and developing people. The Chief Information Officer reports directly to the Chief Executive Officer and serves as a member of the Executive Leadership Team. The role partners closely with Presidents, Business Unit leaders, and shared services functions across all regions. This position can be located in the Los Angeles, Denver, or Chicago metro areas. Key Responsibilities Own enterprise technology strategy and a multi-year roadmap aligned to business strategy, prioritizing and sequencing technology demand so major investments have clear owners, business cases, and defined results, and positioning technology as a trusted partner that drives measurable outcomes across all business functions and regions, spanning construction operations and corporate shared services, enabling technology to improve how the company wins work, executes projects, and develops people. Build, lead, and develop a high-performing technology organization, attracting and retaining talent and shaping a culture of accountability, service, and partnership, and designing the operating model and sourcing mix, keeping strategy, architecture, and risk in-house while using co-sourced delivery and managed services to scale efficiently. Rationalize and evolve the enterprise application and platform portfolio, establishing clear business process ownership, IT platform ownership, integration architecture, and vendor governance across construction and corporate systems, and lead the change management, education, and training, developed with affected departments, that drives adoption as platforms transition and continue to evolve. Establish data as a trusted enterprise asset, creating the governance, ownership, and architecture required for reliable reporting, and champion the responsible, practical adoption of automation and artificial intelligence that advances the business. Own the cybersecurity strategy, risk posture, incident response readiness, and regulatory compliance, including the controls and certifications needed to pursue work in regulated and government markets. Maintain resilient, well-managed infrastructure, end-user computing, and field technology, including reliable office/jobsite connectivity, networks, and devices deployed and supported from project startup through closeout. Set technology governance and service management standards that deliver consistent, high quality support and disciplined, transparent investment, and advise executive leadership and the Board of Directors on technology strategy, enterprise and cybersecurity risk, and major investments on a defined cadence. Skills, Knowledge and Expertise Proven ability to lead enterprise technology organizations spanning applications, data, infrastructure, and cybersecurity, using a blend of internal talent and strategic sourcing partners. Command of cybersecurity risk management, identity, architecture, and compliance frameworks. Experience leading infrastructure modernization, cloud strategy, data and analytics, and application portfolio rationalization at scale. Clear vision for the practical application, deployment and adoption of automation and artificial intelligence to advance business strategy. Working knowledge of construction, project-based, and corporate technology stack, including ERP, field operations, and project management platforms and the integration between them. Proven ability to build, scale, and develop high-performing technology teams, including hiring, organizational design, and culture building. Track record of translating business strategy into a technology roadmap that delivers measurable enterprise value. Strong financial acumen with experience managing technology budgets, vendor contracts, and investment portfolios with transparency and accountability. Ability to design and scale a technology operating model that flexes to the demands of a growing, multi-region construction organization. Experience leading organizational change management and technology adoption, including communication, training, and enablement, across a distributed workforce. Clear, direct communicator who builds trust with executive leadership and regional teams. Strong relationship builder through direct engagement and field presence, not email-only leadership. Pragmatic operator who can set enterprise standards and earn credibility with field, operations, and shared services leaders. Able to translate complex technical matters into clear executive narratives and to build cross-functional buy-in for change and adoption across a decentralized organization. Personal High integrity, accountability, and ownership. Self-motivated, decisive, and forward thinking. Invests in people and brings out the best in a team. Resilient and adaptable while leading in a growing organization. Bachelor’s degree in a technology, engineering, business, or related field, or equivalent experience. Advanced degree or business credential a plus. 15 years of progressive technology leadership, including senior responsibility for enterprise technology in a multi-site organization. Demonstrated success building and developing high-performing technology teams and organizations. Proven experience transforming IT functions into business-aligned, governed, service-oriented technology organizations. Track record modernizing technology operating models, including internal / co-sourced / managed services models, with measurable improvements in service quality, delivery capacity, risk posture, and cost transparency. Strong vendor and partner governance capability, including contracting, performance management, and value realization. Demonstrated ability to partner with operations leaders in construction or a closely related project-based industry. AEC experience preferred. Benefits Hybrid role based at a primary office, with a standard Monday through Friday schedule. Regular travel to regional offices and active jobsites to build adoption and stay close to the work. 100% ESOP Competitive Pay Bonus Program Medical/Dental/Vision Insurance PTO/Sick 100% Life Insurance 401(K) with Match Student Debt Program Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions. Work Environment While performing the duties of this job, the employee regularly works on-site at the construction work site where the employee is exposed to moving mechanical parts, high precarious places, fumes or airborne particles, outside weather conditions and risk of electrical shock. The noise in these work environments is usually moderate to very loud. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, national origin, disability, or status as a protected veteran. J-18808-Ljbffr

Head of Compliance, Gemini Galactic Markets, LLC (Miami)

About the Company Gemini is a global crypto and Web3 platform founded by Cameron and Tyler Winklevoss in 2014, offering a wide range of simple, reliable, and secure crypto products and services to individuals and institutions in over 70 countries. Our mission is to unlock the next era of financial, creative, and personal freedom by providing trusted access to the decentralized future. We envision a world where crypto reshapes the global financial system, internet, and money to create greater choice, independence, and opportunity for all — bridging traditional finance with the emerging cryptoeconomy in a way that is more open, fair, and secure. As a publicly traded company, Gemini is poised to accelerate this vision with greater scale, reach, and impact. The Department: Compliance The Compliance Team at Gemini is dedicated to managing the next generation of compliance risk in a complex and evolving regulatory environment. We are a diverse group of technology, legal, and operational professionals who develop new approaches to solving classic problems using cutting edge tools and processes. The Role: Head of Compliance, Gemini Galactic Markets, LLC Gemini is seeking a dynamic self-starter to lead our broker dealer and future commission merchant compliance program. This role requires deep expertise across federal securities and commodities regulation, SEC, FINRA, CFTC, and NFA, with hands‑on experience building and running compliance programs at a retail‑facing brokerage and FCM. The ideal candidate has strong command of supervisory and surveillance operations across listed securities and derivatives, financial and segregation reporting obligations, and familiarity with digital assets. This role will report into Gemini’s Global Chief Compliance Officer. Responsibilities Provide compliance advisory and support to the broker‑dealer business and oversee the development of the broker‑dealer compliance program Oversee the FCM compliance program, including the firm’s risk management program and annual CCO report Oversee daily customer segregation computations and related financial and regulatory filings across both the broker‑dealer and FCM Supervise trade and market surveillance across the firm’s securities and derivatives products Serve as the primary point of contact for FINRA, NFA, SEC, and CFTC exams and inquiries Maintain the firm’s AML program covering both broker‑dealer and FCM activities Draft, maintain, and implement Written Supervisory Procedures and other internal policies and procedures Collaborate cross‑functionally with technology, product, and legal teams on trading system operations to ensure compliance with regulation and regulatory expectations Advise on core compliance matters including registrations, employee trading, outside business activities, and continuing education requirements Review and approve advertising, marketing, and sales materials Minimum Qualifications BA/BS degree Active FINRA Series 7, 63, and 24 licenses; NFA Series 3 (or ability to obtain within 120 days of hire) 10 years of securities and/or commodities regulatory compliance experience Deep expertise in broker‑dealer and/or FCM operations and the associated regulatory frameworks Strong understanding of FINRA, SEC, CFTC, and NFA compliance requirements Comfort working in a technology‑forward environment Superior writing skills, including the ability to analyze and assess large amounts of information into succinct responses Authorization to work in the United States and fluency in English Preferred Qualifications Advanced degree/certifications, e.g. JD, MBA Familiarity with virtual currencies, digital transfer platforms, ATS Strong cross‑functional collaboration skills Interest in building the future of compliance and an owner’s mindset to your work Experience with surveillance and supervision across securities and derivatives at a multi‑registrant firm It Pays to Work Here The compensation & benefits package for this role includes: Competitive starting pay A discretionary annual bonus Long‑term incentive in the form of a new hire equity grant Comprehensive health plans 401K with company matching Paid Parental Leave Flexible time off Salary Range The base salary range for this role is between $150,500 - $279,500 in the State of New York, the State of California and the State of Washington. This range is not inclusive of our discretionary bonus or equity package. When determining a candidate’s compensation, we consider a number of factors including skillset, experience, job scope, and current market data. In the United States, we offer a hybrid work approach at our hub offices, balancing the benefits of in‑person collaboration with the flexibility of remote work. Expectations may vary by location and role, so candidates are encouraged to connect with their recruiter to learn more about the specific policy for the role. Employees who do not live near one of our hubs are part of our remote workforce. At Gemini, we strive to build diverse teams that reflect the people we want to empower through our products, and we are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. Equal Opportunity is the Law, and Gemini is proud to be an equal opportunity workplace. If you have a specific need that requires accommodation, please let a member of the People Team know. J-18808-Ljbffr

Senior Director - Marketing & Engagement ACA (Jacksonville)

The Senior Director, Marketing & Engagement ACA is one of the most strategically consequential roles in GuideWell’s Communications, Marketing & Customer Experience (CMX) department. Reporting to the VP, Enterprise Marketing & Acquisition, this leader carries a dual mandate: owning the strategy and execution of GuideWell’s acquisition marketing program, and serving as the standing representative of the entire CMX department to GuideWell’s Government ACA segment. This second dimension of the role is not a coordination function – it is a strategic leadership responsibility. The Senior Director, Marketing & Engagement ACA is the person in the room when ACA segment leaders are working through their biggest business challenges. They are expected to listen with the full breadth of CMX in mind: understanding not just what marketing can do, but what communications, customer experience, brand, and insights can contribute to the solution. They bring that perspective to ACA segment conversations fluently, credibly, and proactively – and then return to CMX to mobilize the right subject matter experts, provide context and strategic direction, and ensure the department delivers as one integrated function. This model requires a leader who is genuinely fluent across all CMX disciplines – not a generalist who knows a little about everything, but a senior practitioner who understands each function deeply enough to ask the right questions, frame the right problems, and give SMEs what they need to do their best work. It also requires someone who can operate in the language of the business: conversant in segment strategy, competitive dynamics, growth targets, and operational realities, and trusted by segment leaders as a true partner rather than a service provider. In parallel, this leader directly leads the ACA Acquisition Strategy & Planning function and oversees Creative & Communications Development, Campaign Execution & Operations, and Sales and Local Market Support – four disciplines that together determine whether GuideWell’s marketing reaches the right people with the right message at the right moment. Key Responsibilities CMX Segment Integration & Enterprise Representation Serve as the consistent, senior CMX presence in all segment leadership meetings, strategy sessions, and business planning forums – representing not just marketing, but the full Communications, Marketing & Customer Experience function. Develop and maintain a deep, current understanding of each segment’s business strategy, competitive pressures, growth targets, operational challenges, and member or customer dynamics – well beyond what is needed to brief a campaign. Speak the language of the business as fluently as the segment leaders themselves. Listen to segment challenges with the breadth of the full CMX capability set in mind – identifying where marketing, communications, customer experience, brand, and insights each have a role to play, and framing integrated solutions rather than single-discipline responses. Translate segment business needs into clear, actionable briefs for CMX subject matter experts – providing the strategic context, business rationale, and high‑level direction that allows each SME to do their best work without needing to attend every segment conversation. Mobilize and orchestrate the right CMX experts – across Communications, Customer Experience, Brand, Insights, and Marketing – for each segment challenge, ensuring the department delivers as one integrated function rather than a collection of independent capabilities. Maintain a real‑time understanding of priorities, capacity, and ongoing work across CMX disciplines, so that segment commitments are made with full awareness of what the department can deliver and when. Serve as the accountability owner for CMX’s commitments to each segment – tracking deliverables, managing expectations, escalating risks, and ensuring the department consistently follows through on what it promises. Build and sustain trusted, peer‑level relationships with segment leaders in Commercial, Government, and Health Services – positioning CMX as a strategic partner that earns a seat at the table because of the value it creates, not because of its organizational role. Proactively bring CMX insight, intelligence, and capability to segments before they ask – identifying opportunities where communications strategy, customer experience improvement, brand investment, or deeper audience insight could accelerate a segment’s goals, and making the case for that investment. Report back to the VP, Enterprise Marketing & Acquisition and the broader CMX leadership team on segment priorities, emerging needs, and strategic opportunities – ensuring the department is always forward‑looking in how it aligns resources and capabilities to business needs. Acquisition Strategy & Planning Develop and lead comprehensive enterprise‑level acquisition marketing strategies across all business segments – individual, employer, Medicare, Medicaid, and ancillary health solutions – aligned to growth targets, brand positioning, and go‑to‑market priorities surfaced through segment engagement. Own audience and segmentation strategy – defining target populations, behavioral profiles, and market prioritization frameworks that focus investment where it will drive the greatest enrollment impact, informed by Insights and VOC data. Lead campaign planning and budgeting processes, ensuring resource allocation is grounded in data, competitive intelligence, and the segment‑specific priorities this leader hears firsthand in business forums. Develop and maintain campaign forecasting models and performance tracking frameworks that provide real‑time visibility into pipeline health and enrollment outcomes. Own tactical strategy across all acquisition channels – translating high‑level objectives into specific channel mix, message prioritization, and execution sequencing in partnership with Media Strategy & Planning. Lead identification and scoping of research initiatives that deepen audience understanding, sharpen competitive positioning, and surface new growth opportunities, in coordination with the Insights team. Serve as the accountable decision‑maker for campaign performance – with the authority and responsibility to make in‑flight adjustments, elevate issues, and drive corrective action when results fall short of targets. Creative & Communications Development Provide creative direction for all acquisition marketing campaigns – setting the strategic and aesthetic vision for how campaigns come to life across direct mail, email, digital, and agent‑facing materials, in alignment with Brand team standards and Communications team narrative. Own messaging strategy across all acquisition tactics – ensuring every piece of communication reflects GuideWell’s brand positioning, speaks to the specific audience and segment, and is calibrated to drive action. Where segment‑specific message adjustments are needed, engage the Brand and Communications SMEs to ensure consistency across all channels and audiences. Oversee compliance review of all marketing materials, partnering with Legal and Compliance teams to ensure adherence to CMS marketing guidelines, state regulations, and internal policy requirements. Oversee translation and adaptation of campaign materials for multicultural and multilingual audiences, including Spanish‑speaking and Caribbean market segments served by Triple‑S and Florida Blue. Lead proofreading and quality oversight processes to ensure all materials are accurate, on‑brand, and error‑free before distribution. Monitor competitive creative activity continuously – tracking how national and regional competitors are showing up in the market and surfacing insights that inform GuideWell’s own creative differentiation. Serve as the primary liaison with Creative teams – briefing, directing, and providing feedback that drives both creative quality and efficient production timelines. Campaign Execution & Operations Oversee the planning, execution, and optimization of direct mail campaigns – including list management, vendor relationships, production timelines, and drop schedule adherence. Oversee email marketing execution – ensuring campaigns are deployed accurately, on schedule, and in alignment with segmentation, compliance, and brand standards. Manage telephone and keycode management programs to ensure tracking, attribution, and reporting integrity across all campaign touchpoints. Oversee agent distribution of campaign materials – ensuring field‑facing assets are accurate, timely, and aligned to sales priorities and local market needs. Own campaign workflows and timelines across all tactics – building and managing integrated production calendars that account for creative development, compliance review, translation, and distribution lead times. Lead creative trafficking for all tactics, ensuring materials move through production and approval efficiently and arrive on time and in the correct format. Serve as the liaison with Digital (landing pages and content pages) and Campaign Management teams – coordinating handoffs and maintaining continuity across channels. Sales & Local Market Support Oversee agent connection and distribution programs – ensuring agents have timely access to campaign materials, market intelligence, sales tools, and enrollment resources. Build and maintain deep local market knowledge across GuideWell’s key geographies – an understanding that directly informs the segment intelligence this leader brings to CMX planning and b

Head of Sales (Boston)

Deligo is a leader in visual AI self‑checkout for the convenience retail industry, trusted by global brands such as Compass, Sodexo, Marks & Spencer, and Spar. We build advanced visual AI developed by a top‑notch machine learning team to recognize food and retail items instantly. No barcodes, no manual scanning—just place your items and tap to pay. The result is a magical experience that saves time by eliminating checkout lines. Role at a glance As Head of Sales, you will partner with the founders and the founding sales team on go‑to‑market strategy, secure lighthouse customers, and build the commercial engine for the company's next phase of growth. You will combine hands‑on enterprise selling with strategic leadership—team development, revenue ownership, and creation of scalable sales playbooks. How you’ll make a difference in the first 12 months Develop a Deep Understanding Deeply understand our segments, geographies, and sales motions Strategy Partner with founders and the founding sales team on go‑to‑market strategy and support Series A fundraising with a credible plan Lead lighthouse deals in US Convenience Retail Personally lead and close first convenience store deals on top of our Verifone partnership Build a pipeline, strategy, and repeatable sales motion for large enterprise chains Sales Leadership Lead and develop the sales team; foster a great sales culture Own EU and US revenue growth—qualified pipeline, consistent execution, forecast accuracy, and revenue targets Develop the Deligo Sales Playbook across segments, geographies, and motions (direct, channel) Grow the sales team across Europe and the US to support our growth objectives What makes you a great fit Early‑Stage Revenue Leadership: successful track record of leading enterprise sales through critical growth stages—ideally $5M→$10M and $10M→$30M ARR. Ability to thrive in ambiguity and fast‑moving early‑stage environments Sales Leadership Experience: 5 years leading enterprise sales teams in a scale‑up with full ownership of revenue targets, pipeline, and forecasting Demonstrated success hiring, developing, and building scalable playbooks and repeatable revenue engines Business Acumen: Ability to deeply understand needs and incentives across customers, partners, and the broader ecosystem—to orchestrate win‑win‑win scenarios Talent Magnet: The best go‑to‑market talent wants to work with you, and you have the network to find them Bonus Industry Knowledge: Experience in retail technology, convenience retail, food service, enterprise SaaS, AI‑driven platforms, or adjacent operational technology sectors is highly preferred Experience working across both U.S. and European markets Strong product intuition and taste Why join us Opportunity to join at a critical growth stage, making a visible impact as we scale in the U.S. market Real influence on how our sales organization, GTM strategy, and overall business evolve A collaborative, ambitious, and transparent culture where ownership and impact are recognized Work closely with experienced founders and a world‑class team building a new category High‑tech equipment Flexible working setup with a hybrid approach and frequent travel to customers Competitive salary and equity package aligned with your impact Details Start: As soon as you are ready Location: US East Coast, preference for Boston / NYC area (relocation support available) Set up: Hybrid Contract: Permanent Travel: Up to 50% Compensation: Competitive package including salary, bonus and equity J-18808-Ljbffr