Compensation - $225K+ OTE. $135K base + 90% commission (60 base/40 variable). Commission is uncapped. Hit 120% of quota and you're walking away with $275K. And this is realistic - not a fantasy number. Location - Must be in EST or CST time zones. Remote eligible for those willing to be in Bethesda, MD office every Monday/Tuesday every other week (= 4 days a month). If you are in Bethesda or the DC area, you'll work in person with the team every Monday, Tuesday, and Thursday and from home on Wednesday and Friday. Benefits - Exceptionally generous PTO. It includes vacation, personal days, care days, sick days, 10 federal holidays and the company closes the last week of the year. Free medical plan (dental and vision covered at high rates). Plus 401(k). About Keep Company Keep Company is on a mission to make human connection an intentional, scalable asset in every workplace. As a venture-backed SaaS platform recognized by Techstars, Forbes, and SHRM, our patented talent platform delivers transformative relationship-based development experiences at leading professional services organizations. With our platform, talent leaders can launch, scale and measure innovative programs, including mentoring, coaching and ERGs, with little admin burden and maximum impact. We’re proud to support 20+ clients in professional services - with zero churn and multiple six-figure contracts. At a time when artificial intelligence is rapidly reshaping how we work, Keep Company is rebuilding the human layer of work, because we believe people are the most important asset that organizations can invest in to strengthen culture, retention, and performance in the moments that matter most. The Role As a Keep Company Founding Account Executive, you will drive new business in the mid-market segment through prospecting, deal and pipeline management, and closing. You will be part of an elite, professional, and rapidly growing team that succeeds through collaboration, tenacity, and constant improvement. This is Keep Company's first sales hire, which means you're not just filling a role- you're building the foundation. You'll work directly with the CEO to turn early traction into repeatable revenue and establish the sales motion that future hires will learn from. This isn't for someone who needs structure handed to them. It's for someone who thrives creating it. Responsibilities - Engage prospects at a senior executive level (Chief Human Resource Officers, Chief Talent Officers, and Directors of Professional Development) to pursue and close new customers in the legal and professional services sectors - Conduct outbound prospecting to fill your pipeline with qualified sales opportunities as well as handling inbound opportunities - Tightly manage all prospects through the sales funnel in Hubspot - Consistently achieve revenue targets by applying modern sales techniques and processes to efficiently manage sales opportunities through your funnel to a successful close - Partner directly with the CEO to build and refine the sales motion, including processes, language, and playbooks - Use your creativity and tenacity to develop and improve how we target and penetrate new market segments What You Bring Skills & Attributes - You're a hunter: Net new logos are your scorecard and you build the pipeline yourself - You're gritty: You know what it means to grind through a long, complex cycle with a skeptical buyer and come out the other side with a signed contract - You're sharp and curious: You grasp complex concepts quickly, ask better questions than anyone in the room, and genuinely want to understand why - why the prospect is in pain, why a deal stalled, why something worked - You own your outcomes: Good quarter or bad, you know exactly what happened and why. You don't make excuses. You make adjustments - You're coachable: You take feedback well - not because you're passive, but because you're wired for constant improvement. - You read the room: You're self-aware, politically sharp, and keenly attuned to how you're being perceived. You know when to push, when to pause, and when to bring in a champion Required Experience - 5+ years of B2B sales experience in a hunting role focused on net new business - 2+ years of experience selling complex software solutions with multi-month sales cycles - Demonstrable track record of above-target performance, especially in a startup or early-stage environment - Experience earning access to and influencing senior executive buyers Nice to Have - Some traditional sales training (you know what good process looks like) with real startup DNA (you know how to move without a playbook) - 4-year degree from a credible institution with strong performance, or equivalent real-world experience - Solid extracurricular track record- sports, leadership, performance- something that shows you know how to compete Why Keep Company - Earn uncapped commission as you sell a new and disruptive technology into a huge market - A direct line to the CEO and real influence over how this company goes to market - A fast-paced and collaborative environment where we leverage the latest technology and keep getting better - An opportunity as an early team member to help shape the direction and culture of the company - Competitive compensation and opportunity for advancement- a true meritocracy where performance is recognized and rewarded. Compensation is structured 60/40 (base/variable) with OTE of $225k+, uncapped - Comprehensive benefits: Health (medical, dental & vision), 401(k), and flexible PTO - Hybrid work schedule: Three days per week in our Bethesda, MD office How to Apply Some candidates may see the list above and feel discouraged because they don't match all the items. The data says this is especially true of traditionally underrepresented communities. Please apply anyway: there's a good chance you have valuable skills. We are committed to building an equitable environment, and we're taking steps to meet that commitment. If you're excited about making a tangible impact in a mission-driven organization and across the working world, we'd love to hear from you.

• Create detailed business plans designed to attain predetermined goals and quotas • Manage the entire sales cycle from securing an opportunity to closing a deal • Unearth new sales opportunities through networking and turn them into long-term partnerships • Provide business, technical, and product knowledge in support of post sales activities in order to ensure customer satisfaction • Provide professional after-sales support to maximize customer loyalty • Respond to complaints and resolve issues to the customer’s satisfaction and to maintain the company’s reputation • Negotiate agreements and keep records of sales and data in CRM • Build and leverage channel partner relationships with NetSuite AEs and other stakeholders Deliver and reliably manage a sound pipeline of opportunity • Generate SOWs to precisely incorporate scope collected from solution architects and present the SOWs to customers • Meet and exceed monthly and yearly targets for sales and recurring revenue from existing customers • Responsible for lead and pipeline generation targets outside partner channel • Travel as needed to client sites and conferences for relationship-building activities

• Develop and secure new partnerships with credit unions and banks throughout the Central and Western US region. • Manage the full sales cycle—from territory planning and prospecting through solution presentations, negotiations, and closing. • Build and manage a healthy, active sales pipeline, continually sourcing and engaging new business prospects to exceed sales targets. • Establish credibility and trust by understanding client needs and conveying the value of our full suite of lending solutions, including education and home improvement lending products. • Stay informed about competitive activity and evolving industry trends, providing insights to leadership. • Attend regional banking and credit union association events to drive lead generation and networking. • Deliver effective product demonstrations and presentations tailored to diverse audiences. • Maintain thorough and accurate updates of all sales activity and opportunities within CRM. • Communicate pipeline status, progress, and market trends to management regularly.

Role Description We are building an AI-native Data Cloud and need a VP of Engineering who owns architecture, execution, and business outcomes end-to-end. The buck stops with this role for platform reliability, developer experience, and Data Cloud adoption. DigitalOcean’s Data Cloud will power AI applications end-to-end—from data ingestion to real-time inference—enabling developers to build production-grade RAG systems, AI agents, and analytics workflows on a single, integrated platform. This role is responsible for delivering that platform by leveraging and extending DigitalOcean’s existing infrastructure, PaaS, and AI capabilities. This is not a traditional data platform role. You will define and execute the strategy to move DigitalOcean up the stack—from infrastructure provider to a differentiated AI application and inference platform. Success will be measured through roadmap velocity, system reliability, developer adoption, and measurable business impact. We are looking for a leader who translates strategy into shipped systems, with clear accountability for outcomes. What You’ll Do: - Data Cloud Platform - Architecture and delivery of a unified platform spanning: - Ingestion (connectors, CDC, streaming) - Storage (object, OLAP, vector, graph) - Processing (ELT pipelines, real-time and batch) - Query & analytics (SQL, hybrid search, RAG) - Governance (catalog, lineage, versioning, access control) - AI-Native Capabilities - Knowledgebase-as-a-Service (RAG pipelines) - Vector and hybrid retrieval systems - Feature and embedding pipelines - Real-time inference data paths - Product & Execution - Deliver GA-grade services with strong SLAs, cost efficiency, and simplicity - Drive roadmap aligned to Digital Native Enterprise (DNE) customers - Establish and manage clear metrics: adoption, retention, ARPU, performance, reliability - Organizational Leadership - Build and scale a high-performing global organization (US and India) - Implement single-threaded ownership (STO) across services - Partner deeply with Product, GTM, and Platform Engineering What Success Looks Like (12 months) - Launch a cohesive Data Cloud platform—not a collection of fragmented services - Achieve meaningful adoption across AI-native workloads (RAG, inference, analytics) - Reduce developer time-to-value from weeks to hours - Establish clear differentiation versus hyperscalers on simplicity and cost Qualifications - Proven track record of building and operating cloud-scale data platforms (OLAP, lakehouse, streaming, or ML systems), with strong architectural judgment across storage, processing, and query layers - Experience integrating open-source ecosystems (e.g., Spark, Airflow, dbt) into managed cloud services at scale - Experience with AI/ML data pipelines (feature stores, embeddings, RAG) - Demonstrated ability to operate in ambiguity, make high-quality decisions with incomplete data, and drive multi-quarter execution with measurable outcomes - Proven experience scaling engineering organizations and delivering under real-world constraints - Critical requirement: You have personally driven complex distributed systems from concept to production—not just managed teams that did. Benefits - We innovate with purpose. - We prioritize career development. - We care about your well-being. - We reward our employees. Compensation Range $279,200.00 - $349,000 *This is a remote role JR: 2026-7683 #LI-Remote Company Description DigitalOcean is an equal-opportunity employer. We do not discriminate on the basis of race, religion, color, ancestry, national origin, caste, sex, sexual orientation, gender, gender identity or expression, age, disability, medical condition, pregnancy, genetic makeup, marital status, or military service. Application Limit: You may apply to a maximum of 3 positions within any 180-day period. This policy promotes better role-candidate matching and encourages thoughtful applications where your qualifications align most strongly.