About Actively AI

Our thesis is that businesses of the future will be powered by agentic human-in-loop-machines that make every business function 10x more efficient.

Actively AI is building that machine for sales & marketing, focused on accelerating pipeline generation. We power the day-to-day for outbound teams at dozens of well-known companies like Navan, Ramp, Verkada, Ironclad, and Justworks.

In addition to top-notch customers that love our product, our team is incredibly high caliber - the co-founders are former Stanford AI researchers and the engineering team comes from Harvard, CMU, Berkeley, Brex, Scale AI, and Google. We're also well-funded with the support of top venture capital firms.

We have a very ambitious product and scaling roadmap, there’s strong market interest in what we are doing, and it’s time to put the foot on the gas. If you get excited by the thought of working really hard on these kinds of problems with a high caliber team, then Actively AI is the right place for you.

Job Description

Actively AI is looking for a strategic, cross-functional operator to own and optimize our proof-of-value (POV) process. As an Enterprise AI Success Lead (Pre-Sales), you’ll be responsible for delivering high-quality, insight-rich, and conversion-ready pilot experiences for every enterprise prospect.

This role sits at the intersection of Sales, RevOps, Product, and Data — owning driving cross-functional alignment internally + externally to ensure maximum value is recognized as prospects leverage our custom built models as a part of their GTM strategy. Your goal is to create repeatable, data-informed, and stakeholder-aligned POC experiences that drive consistency and conversion at scale.

What You’ll Do

Own and optimize the end-to-end POC process, ensuring enterprise prospects experience a polished, strategic, and high-conversion pilot.
Act as the primary champion for enablement across all levels of the buyer org — including end users, managers, RevOps leads, and executive sponsors.
Coordinate internal execution across Sales, FDEs, Product, RevOps, and Engineering, while aligning with external stakeholders such as CROs, Enablement, and GTM operators.
Lead training sessions to ensure that the product is meeting user needs and having concrete impact on their operations
Deliver high-quality meetings, training, and executive updates — tailored by stakeholder type and framed in operational, ROI-driven language.
Proactively manage POV timelines, milestones, risk, and results tracking — ensuring no detail is dropped across multiple concurrent pilots.
Standardize workflows, documentation, success criteria, and communication templates to ensure scalable, repeatable execution.
Analyze pilot performance using internal product signals and customer behavior (adoption, usage, feedback).
Translate insights into actionable, strategic recommendations — especially for RevOps and CRO-level stakeholders.
Own cross functional alignment on conversion rate optimization across the POV funnel, including reporting, goal setting, and weekly performance reviews w/AEs and FDEs.
Maintain strict objectivity and consistency — distinct from the AE or FDE, your focus is on process quality and conversion, not deal pressure.

What You Bring

3+ years of experience in Revenue Operations, Customer Success, onboarding, consulting, or a related customer-facing role in B2B SaaS.
Background in systems, data, and GTM workflows — able to bridge between internal teams and buyer-side stakeholders.
Proven track record of managing complex, multi-stakeholder implementations or POVs with a structured project management approach.
Experience working directly with executive buyers (ex. CROs, SVPs) as well as frontline users (AEs, SDRs), tailoring communication for each.
Analytical mindset — comfortable interpreting platform usage, identifying leading indicators, and tracking success metrics.
Strong communicator who can "talk CRO" and “talk end user” with equal fluency.
Familiarity with CRMs, sales enablement platforms, and analytics tools to support operational reporting.
Excitement about AI — able to speak credibly about product capabilities with technical and non-technical audiences alike.
Objective, neutral, and rigorously execution-minded — success is measured by repeatability, consistency, and conversion.

Benefits:

🚀 Competitive Early-Stage Equity
⚕ Health, Dental, Vision Coverage
💡 Unlimited PTO + Recharge Days
🍽️ Catered Lunch on Tuesday & Friday w/ Dinners Everyday!
🍿 Fully Stock Kitchen
💻 Cutting-Edge Tech & Tools
🌴 Annual Off-sites & Monthly Events
🚆 Commuter Benefits
🏢 Cozy Office in NYC

The base salary range for this full-time position based in New York is: $130,000 - $160,000. This position is eligible for incentive stock options, subject to the terms of Actively AI's applicable plans. This position is also eligible for variable compensation and is subject to personal performance, company performance, and the terms of Actively AI’s applicable plans. Actively AI offers the following benefits for this position, subject to applicable eligibility requirements: health, dental and vision insurance, retirement benefits, and unlimited PTO. Additionally, this role may be eligible for additional benefits such as a commuter stipend. Please discuss with your recruiter for more information.

Note on Pay Transparency:
Actively AI provides an estimate of the compensation for roles that may be hired as required by state regulations. Compensation may vary based on (a) location, as Actively AI factors in specific location when benchmarking compensation for most roles; (b) individual candidate skills and qualifications; and (c) individual candidate experience. Additionally, Actively AI leverages current market data to determine compensation, so posted compensation figures are subject to change as new market data becomes available. The salary, other compensation, and benefits information is accurate as of the date of this posting. Actively.ai reserves the right to modify this information at any time, subject to applicable law.

Actively AI is committed to equal treatment and opportunity in all aspects of recruitment, selection, and employment without regard to gender, race, religion, national origin, ethnicity, disability, gender identity/expression, sexual orientation, veteran or military status, or any other category protected under the law. Actively AI is an equal opportunity employer; committed to a community of inclusion, and an environment free from discrimination, harassment, and retaliation.