Head of AI Sales - Enterprise
Waffle Labs
An MIT spinoff, Waffle Labs is an AI research company at the forefront of developing the world’s most advanced Large Data Model. Powered by proprietary and large-scale anonymized data from various industries, Waffle Labs uncovers transformative insights. Founded in 2018, the company is supported by renowned partners, including Sony Innovation Fund, Barclays, Techstars, and BetterLabs Ventures. What You Will Do Own the full enterprise revenue motion — from pipeline strategy through contract execution — targeting Fortune 500 and high-growth technology companies Drive 7-figure and multi-year contract negotiations with sophisticated procurement, legal, and executive stakeholders Partner closely with Product and Engineering to translate customer needs into roadmap priorities and winning proposals Build and refine sales playbooks, pricing frameworks, and competitive positioning strategies Report directly to the CEO and Chief Data Scientist with full visibility into company strategy What You Bring You are a doer. 7+ years of enterprise sales experience, including 3+ years in a leadership role at an AI, ML, or data infrastructure company Demonstrated track record of closing multiple $1M+ contracts with Fortune 500 or major public‑sector organizations Prior experience selling data annotation, synthetic data, or ML training data products Deep functional understanding of machine learning workflows — model training, data pipelines, MLOps, and the infrastructure that supports them Ability to engage credibly at the CTO, VP of AI/ML, and Chief Data Officer level Experience navigating long, complex sales cycles (6–18 months) with multiple stakeholders and procurement gatekeepers Strong analytical instincts — you're comfortable in CRM and building your own pipeline forecasts This is a Boston-based position. Nice to Have Relationships within AI/ML teams at major cloud providers, financial institutions, and/or retail Background in technical pre‑sales or solutions engineering Incentives Competitive package + 100% healthcare and dental AMAZING commission structure Attractive equity package Must be authorized to work in the US. No visa sponsorship. #J-18808-Ljbffr Waffle Labs
- ...Cambridge, MA, is seeking an experienced VP of Sales to own and build our direct selling... ...a large greenfield market. You will lead enterprise and velocity sellers, collaborate with pre... ...new accounts while aligning with product, marketing, and #J-18808-Ljbffr Manifold AISuggested
- A leading AI platform provider in Boston is seeking a Regional Vice President of Enterprise Sales to guide a team of Enterprise Sales Directors. This role includes managing sales operations, coaching teams, and developing growth strategies for customer buy-in. The ideal...Suggested
- Maven AGI in Boston, MA, is seeking a Regional Vice President of Sales to lead our Enterprise Account Executives, build a regional plan, and accelerate growth in a fast‑moving startup environment. You will own revenue targets, drive long‑term strategic deals across Fortune...Suggested
$180k - $240k
As a Director, Enterprise Sales Engineering, you will lead a team of frontline leaders, driving account strategy, deal execution, operational... ...outcomes especially in a world increasingly dominated by Agentic AI.Partner confidently with senior Sales leadership on regional...SuggestedWork at office- ...represents a leading global pioneer in advanced malware analysis and threat intelligence. We seek a Head of Sales USA to lead, coach, and scale a high-performing team across enterprise and federal sectors, delivering strategic go-to-market execution and hands-on deal support....Suggested
- ALTEN Technology USA is seeking a Vice President of Sales - Aerospace & Defense to lead North American growth, identifying and closing enterprise opportunities and building executive-level relationships with major aerospace, aviation, and defense players. You will drive...
- ...pioneering technology company in Boston is seeking a Head of Commercial to drive the go-to-market strategy and build a scalable sales engine. The ideal candidate must have over a... .... Responsibilities encompass closing enterprise sales deals, defining commercial strategy,...
- Waffle Labs, an AI research company in Boston, is seeking an experienced sales leader to own enterprise revenue operations. The ideal candidate has over 7 years of sales experience, including substantial contracts with Fortune 500 companies. Responsibilities include pipeline...Contract work
- ...Userlane Userlane is a software adoption platform that shows enterprises whether their software and AI investments are actually working. Our team works with... ...domain knowledge, rather than general enterprise sales experience alone. Responsibilities Named US healthcare...Base plus commissionFull timeContract workImmediate start
Userlane
Boston, MAa month ago $161k - $244k
Personify Health seeks an experienced Regional VP of Enterprise Sales to lead and scale a high-performing team across HR, Benefits, and Talent Management. This remote role with up to 50% travel focuses on strategic territory planning and results-driven leadership. You...Remote job- VMRay in the United States is seeking a strategic Enterprise Sales Leader to drive nationwide growth across Enterprise, MSSP, BFSI, and government sectors. You will lead a high-performing team, shape pipeline, forecast accurately, and close complex, high-value deals with...
- RSM US LLP is seeking a Business Development Director for Microsoft Dynamics 365 Enterprise to lead the sales process from prospecting to closure across upper/middle and enterprise markets. You will drive opportunity strategy, coordinate teams, and build strong client...
- SmartCOP Inc. is seeking a Director of Sales to lead our New Name acquisition strategy and build a high-performing enterprise sales team targeting the public sector. You will own the end-to-end sales cycle for CAD, RMS, and JMS solutions, drive net bookings, and develop...Remote job
$275k - $315k
...great global utility, just like electricity. Role Description: AI Sales Director, East Role Purpose Wasabi Technologies is looking for... ..., target, and engage AI startups, model developers, and enterprise AI teams with high-performance storage needs. Leverage channel...Local area- Kinaxis is seeking a Regional Vice President, Sales to lead a sales team focused on driving success in supply chain management solutions... ...a minimum of ten years in sales with experience in managing enterprise-level solutions. This position is fully remote, allowing for...Remote job
- Veeva Systems is seeking a Director of Sales for QualityOne Extended Industries to lead a high‑performing Account Partner team selling global enterprise eQMS solutions to large manufacturers. You will drive revenue targets, coach complex deal strategy, and build long‑term...
$400k
...Description This is a fully remote opportunity. Gradient AI: Gradient AI is revolutionizing Group Health and P&C insurance... ...About the Role: We are searching for a results-driven Enterprise Sales Director – Health to join our growing team and lead enterprise...Contract workRemote workWork from homeFlexible hoursGradient AI
Boston, MA7 days ago- Coder is seeking a Regional Vice President of Enterprise Sales to lead a team selling into high-value accounts and strategic initiatives. You... ..., and deal strategy, with a focus on regulated industries and AI-enabled modernization projects. Travel is required quarterly....
$200k
Your role at Dynatrace The Partner Sales Director - AI Alliances, App Builders & SaaS owns the broadest and most commercially layered segment... ..., Retool etc and AI-Native SaaS Applications: Production enterprise AI applications like Harvey (legal AI), Glean (enterprise...Worldwide- Veeva Systems is seeking a Director of Sales, QualityOne Extended Industries to lead a high‑performing team of Account Partners focused on selling global enterprise eQMS solutions to large manufacturers. This role is accountable for achieving regional revenue targets and...
$130k - $150k
Overview Seismic is the global leader in AI‑powered enablement, empowering go‑to‑market leaders to... .... Who you are 7+ years of solution sales experience with a history of driving, managing and closing enterprise deals Experience selling software (cloud/SaaS)...Remote job- Infoblox is seeking a Director of Sales for the New Logo team in the East region. Lead and mentor the Enterprise Account Executives to grow revenues, align sales initiatives with marketing and channel partners, and drive a cohesive, high-impact go-to-market. You will own...
- Epsilon is seeking a Director, Sales (New Business) - MarTech to lead and close complex, high-value MarTech and AdTech deals across Fortune 1000 organizations. This role is designed for proven enterprise sellers who consistently exceed quota and thrive in multi-stakeholder...
- Pointr is seeking a Director of Sales Excellence in Boston to elevate our enterprise sales motion. This senior player‑coach role partners with Customer Advocates to drive qualification, deal strategy, and forecast discipline across high‑value opportunities. You will shape...
- Gradient AI is seeking an Enterprise Sales Director to lead sales efforts across the health insurance ecosystem. This individual will own the full sales cycle, leveraging their extensive experience and relationships within the health insurance space. The ideal candidate...Remote job
- Benchling, a biotech AI platform, seeks an Enterprise Account Executive to drive new and renewal business within top pharma accounts. You will build relationships across IT, Science/R&D, and Data Science, expand the customer base, and ensure successful outcomes through...Remote job
- Harmony is hiring an Enterprise Sales Representative to own the full sales cycle in the US East region, including Boston and DMV areas. You will engage IT, HR, and Operations buyers, translating AI automation capabilities into measurable business outcomes to drive revenue...
- A leading cybersecurity vendor is seeking an Enterprise Account Executive to cover the Northeast region. This... ...position involves driving full-cycle enterprise sales, developing territory plans, and educating customers on AI data security. The ideal candidate will have 7-1...
- ...drive market expansion in the US. This role involves managing sales cycles, identifying new business opportunities, and collaborating... ...of the retail industry, and a proven track record in selling AI enterprise software. This is a full-time position. #J-18808-Ljbffr Snatch...Full time
- Building GTM teams with VC backed Cyber Security vendors across North America and EMEA! Enterprise Account Executive - AI Data Security (Seed Stage Vendor) I am hiring the #2 Enterprise Sales hire to cover the Northeast region. This is a rare ground‑floor opportunity to own...
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