At AI Squared, our vision is to foster widespread AI adoption by embedding AI insights directly into mission-critical business applications and everyday workflows. By leveraging AI Squared’s platform, organizations can access and integrate any data or machine-learning insight directly into their web-based business applications – leading to data-driven decisions and ML-powered innovation.
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About the Role:
We are looking for a highly motivated Sales Engineer with a strong background in AI infrastructure to join our dynamic team. In this role, you will play a critical part in driving enterprise sales, supporting both pre-sales and post-sales activities, and partnering closely with account executives to deliver cutting-edge solutions to our clients.
Key Responsibilities:
Qualifications:
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Position Overview
We are seeking a dynamic and results-driven Strategic Account Executive to focus on acquiring new customers and expanding our market presence in the enterprise segment. In this role, you will help large, complex organizations adopt and scale our cutting-edge data, AI, and analytics platform to drive transformation at scale. You will own the entire sales cycle, from strategic prospecting to contract execution and work closely with senior technical and business stakeholders to deliver high-impact, tailored solutions. This role is pivotal in driving revenue growth through the pursuit, development, and closure of high-value enterprise opportunities. The ideal candidate thrives in highly complex sales environments, is trusted at the executive level, and knows how to move big deals forward.
Key Responsibilities
Enterprise New Business Development: Identify, qualify, and pursue large-scale enterprise opportunities to secure new logos and major expansion deals.
Solution Selling: Use a consultative, value-based approach to diagnose enterprise challenges and align our platform to business and technical objectives.
Executive Engagement: Build deep relationships with C-suite and VP-level leaders including CIOs, CTOs, CDOs, and business unit heads.
Strategic Pipeline Management: Develop and manage a strong, high-value pipeline with clear deal strategy, close plans, and accurate forecasting.
Targeted Prospecting: Execute strategic outreach including account-based selling, executive-level networking, and event-based engagement.
Complex Sales Cycle Management: Lead all phases of multi-stakeholder, multi-month enterprise sales cycles including discovery, demos, proposals, business cases, negotiations, and closure.
Market & Account Intelligence: Monitor industry trends, account priorities, budgets, and competitive activity to identify and shape opportunities.
Cross-Functional Leadership: Partner with marketing, product, customer success, and leadership to support enterprise deal strategy and post-sale success.
CRM Discipline: Maintain detailed and accurate activity, pipeline, and account information in CRM systems (Salesforce/HubSpot or equivalent).
Revenue Performance: Consistently meet or exceed enterprise quota targets and key performance indicators.
Qualifications
Location: Remote with a high preference for candidates within the NYC & Chicago metro area(s).
Experience
10+ years of enterprise sales experience with a strong record of closing large, complex deals (6–7+ figure ACVs), preferably selling SaaS, data, AI, or analytics platforms.
Education
Bachelor’s degree in business, marketing, or a related field; MBA is a plus.
Skills
Proven ability to prospect, develop, and close enterprise level opportunities
Experience managing full cycle, multi stakeholder enterprise sales motions
Strong command of structured sales methodologies (MEDDICC, Challenger, Spin, etc.)
Executive level communication, presentation, and influence skills
Proven ability to navigate complex buying groups and long procurement cycles
Expertise in building business cases and articulating ROI at scale
Comfortable delivering executive-level demos and strategy sessions
Strong negotiation and closing abilities, including contract and pricing strategy
Deep familiarity with SaaS models, multi-year contracts, and expansion planning
Advanced CRM, pipeline management, and forecasting capabilities
Ability to manage a small number of high-impact accounts with precision and discipline
Attributes
Confident, strategic, and credible with senior executives
Results-obsessed with a strong sense of urgency and ownership
Highly resilient and comfortable operating in ambiguity and long sales cycles
Strategic thinker with the ability to execute at a tactical level
Organized, disciplined, and detail-oriented with strong follow-through
Curious, commercially sharp, and continuously improving
Comfortable being the quarterback for large, cross-functional deal teams
Polished, professional, and trusted both internally and externally
Collaborative but fully capable of running complex deals independently
Composed under pressure and able to keep momentum through setbacks
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Position Overview
We are seeking a dynamic and results-driven Strategic Account Executive to focus on acquiring new customers and expanding our market presence in the mid-market segment. In this role, you will focus on helping organizations adopt and leverage our cutting-edge data, AI, and analytics platform to transform their business. You will own the entire sales cycle, from prospecting to closing, and work closely with technical and business stakeholders to deliver innovative, high-value solutions. This role is pivotal in driving revenue growth by identifying, targeting, and closing new business opportunities. The ideal candidate thrives on building relationships, navigating complex sales cycles, and delivering tailored solutions that address prospective clients' needs.
Key Responsibilities
New Business Development: Proactively identify and pursue prospects and new business opportunities to secure new logos, expanding the company’s customer base.
Solution Selling: Use a consultative approach to understand prospective clients’ business challenges and articulate the value of our platform in solving their data and AI needs.
Executive Engagement: Build relationships with senior decision-makers, including CIOs, CTOs, and data and business leaders, to establish trust and influence decision-making.
Pipeline Management: Build and manage a robust sales pipeline, ensuring consistent achievement of sales targets and KPIs.
Prospecting & Outreach: Utilize various tools and strategies (e.g., cold outreach, networking, events) to engage potential customers and qualify leads.
Consultative Selling: Understand prospective clients' unique challenges and objectives, delivering tailored solutions that demonstrate clear value and ROI.
Sales Cycle Management: Manage the entire sales process, including prospecting, discovery, solution presentation, negotiation, and contract closing.
Market Intelligence: Stay informed about industry trends, competitors, and market conditions to identify opportunities and position the company’s offerings effectively.
Collaboration: Partner with marketing, product, and other internal teams to create compelling go-to-market strategies and ensure smooth onboarding for new clients.
CRM Mastery: Maintain accurate records of prospect interactions, sales activities, and progress in CRM systems (e.g., Salesforce, HubSpot).
Metrics & Reporting: Consistently achieve or exceed sales quotas and report on progress, pipeline, and forecast accuracy.
Qualifications
Location: Remote but with a high preference to candidates located within the NYC & Chicago metro area(s)
Experience
10+ years in sales or business development, with a proven track record of acquiring new clients, preferably selling SaaS, data, AI, or analytics solutions into the mid-market.
Education
Bachelor’s degree in business, marketing, or a related field; MBA is a plus.
Skills
Strong prospecting and lead generation expertise, including cold calling, outbound email, LinkedIn/social selling, and event-based networking
Experience managing high-velocity mid-market sales cycles from first touch to signed contract
Ability to effectively qualify opportunities using structured methodologies (e.g., MEDDICC, BANT, or similar)
Excellent communication and storytelling skills, with the ability to present to both technical and non-technical audiences
Strong negotiation and objection-handling abilities
Comfort running product demos and solution presentations independently
Experience selling consultative, value-based solutions with clear ROI articulation
Familiarity with SaaS business models, subscription-based pricing, and expansion/upsell strategies
Strong working knowledge of CRM systems, pipeline management, forecasting, and reporting
Ability to manage multiple deals in parallel while maintaining accuracy and speed
Attributes
Highly motivated, target-driven professional who takes full ownership of outcomes
Results-oriented with a healthy competitive edge and a bias for action
Self-starter who thrives in autonomy and doesn’t need to be micromanaged
Resilient and persistent — handles rejection without losing momentum or confidence
Organized, detail-oriented, and disciplined in follow-through
Curious, coachable, and always looking to improve performance
Adaptable and flexible in evolving, high-growth environments
Strong sense of accountability, professionalism, and integrity
Collaborative team player who also knows how to run their own book of business
Comfortable with ambiguity and able to make smart decisions with limited information
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Who are we looking for?
We are seeking a talented and experienced Backend Engineer (SDE – 2) to join our distributed team. In this role, you will be responsible for designing, developing, and maintaining scalable and secure backend systems. As a key contributor, you will collaborate with engineers, product managers, and stakeholders to ensure backend infrastructure delivers an exceptional user experience while maintaining high performance and reliability.
Responsibilities:
Requirements:
Preferred:
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Ready to apply?
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Ready to apply?
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Position Overview
We are seeking a skilled and proactive QA SDET – 2 to join our distribution team. This isn't your typical "just run the test cases" role. We need someone who can deeply understand our AI ecosystem, take ownership of quality across the product, and drive testing excellence through automation and first-principles thinking. You'll work autonomously in a remote environment, requiring strong self-direction, excellent communication, and genuine curiosity about both the product and the testing craft.
You will be responsible for
Requirements
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Position Overview
We’re looking for a results-driven Account Executive to grow our federal business and expand our footprint across U.S. government agencies. You’ll own the full sales cycle, helping agencies adopt our data, AI, and analytics platform to solve mission-critical challenges. This role requires deep experience navigating federal procurement, building senior-level relationships, and closing complex, high-value deals. You’ll work closely with internal teams and partners to align solutions with agency priorities and deliver measurable impact.
If you thrive in complex environments and know how to turn government interest into signed contracts, this role was built for you.
Key Responsibilities
Federal New Business Development: Identify, qualify, and close new logo opportunities across U.S. federal agencies (civilian, DoD, intelligence, or defense).
Agency Engagement: Build and maintain relationships with key government stakeholders including program managers, contracting officers, CIOs, CTOs, and mission owners.
Solution-Based Selling: Translate mission problems into compelling solutions using our AI and data platform. Show them the “why should I care” in 30 seconds or less.
Pipeline Ownership: Build and manage a qualified federal pipeline, tracking everything from early-stage interest to funded opportunity.
Procurement Navigation: Understand and operate within federal acquisition frameworks (FAR/DFARS, IDIQs, BPAs, GWACs, SBIR/STTR, etc.).
Partner Strategy: Work with government integrators, resellers, and strategic partners to expand reach and accelerate deal flow.
Proposal & RFP Support: Collaborate with internal teams on responses, pricing, positioning, and compliance elements for government bids.
Market Intelligence: Track federal budget cycles, approved programs, agency priorities, and competitor positioning.
CRM & Reporting: Maintain accurate activity, pipeline, and forecasting data in the CRM (Salesforce/HubSpot or equivalent).
Revenue Performance: Consistently meet or exceed federal sales targets and defined KPIs.
Required Qualifications
10+ years in enterprise or federal sales, with direct experience selling into U.S. government agencies
Proven track record of closing 6–7 figure federal deals
Strong understanding of federal procurement processes and contract vehicles
Existing relationships inside federal agencies, integrators, or primes
Exceptional communication, negotiation, and executive presence
Comfortable working complex, multi-stakeholder deals from concept to contract
Experience selling AI, data, analytics, SaaS, or emerging tech into government
Familiarity with DoD, IC, DHS, or civilian agency buying patterns
Active clearance (or ability to obtain one)
Experience working with partners like Booz, Lockheed, Accenture Federal, etc.
Attributes for Success
Competitive and persistent without being annoying
Comfortable operating in ambiguity and long timelines
Highly organized and self-directed
Strategic thinker who can also execute
Takes ownership like it’s their company (because that’s how winners operate)
Ready to apply?
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