Lead – AI GTM Architect & Proof of Value Manager

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 lead-level GTM operator to own our pre-sales enterprise proof-of-value (POV) process while helping design and scale Actively’s own AI-native sales organization.

As Lead, AI GTM Architect & Value Consultant, you’ll deliver high-quality, insight-rich, and conversion-ready pilot experiences for enterprise prospects while building the internal systems that make Actively’s sales team the benchmark for productivity. This is a role for someone who can diagnose GTM problems across companies and design solutions that leverage Actively, complementary tools, and proven strategies.

You’ll work closely with AEs throughout sales cycles, collaborate daily with our Forward Deployed Engineers on model training, integrations, and data workflows, and maintain a dotted-line partnership with our Director of Revenue Operations to ensure internal GTM systems are optimized. In addition, you’ll work hand-in-hand with sales leaders to keep POV execution tightly embedded in the broader sales motion. Alongside the CRO and cofounders, you’ll also innovate on new POV approaches, GTM initiatives, and AI-native operating models.

What You’ll Do

• Lead enterprise POVs end-to-end: onboarding, kickoff, dashboards, milestones, training, and executive briefings.
• Partner directly with AEs on live sales cycles, ensuring POVs accelerate deal velocity and align to prospect success criteria.
• Collaborate daily with Forward Deployed Engineers on integrations, data work, and model training required for POV execution.
• Work closely with the Director of Revenue Operations (dotted line) and sales leaders to align POV execution and GTM system design.
• Diagnose GTM challenges across enterprise prospects and design solutions that incorporate Actively alongside broader GTM strategies.
• Motivate and coordinate internal and customer-side managers and operators to hit deliverables and timelines.
• Troubleshoot and unblock bottlenecks daily, while managing expectations internally and externally.
• Standardize workflows, documentation, and templates to ensure repeatable, scalable POV execution.
• Experiment with tools (including using Actively on Actively) to create leverage for Actively’s GTM org.
• Establish new and creative ways to run POVs and accelerate internal GTM effectiveness.
• Partner closely with the CRO and cofounders on GTM innovation, POV strategy, and AI-native operating models.

What You Bring

• 3–8 years in GTM leadership, RevOps, Sales Engineering, Consulting, or Account Management in B2B SaaS, with preference to Enterprise AI experience.
• Comfort with data and AI: SQL, Python, LLM APIs, and enrichment/data systems.
• Enterprise GTM experience - leading teams, scaling RevOps, or designing workflows at enterprise-grade organizations.
• Proven ability to diagnose GTM problems (outbound performance, AE productivity, funnel conversion, forecasting) and translate them into data-driven solutions — including modeling ROI, CAC efficiency, and productivity lift.
• Drive operational excellence across POVs and GTM initiatives - keeping multiple workstreams, stakeholders, and deliverables moving on time and with precision.
• Bring commercial acumen to POVs - shaping narratives, handling objections, and helping AEs advance deals by positioning Actively’s value with executive buyers.
• Familiarity with CRMs and sales engagement platforms (Salesforce, Outreach, SalesLoft).
• Team leadership or cross-functional management experience a plus — directly managing reports or orchestrating execution across multiple functions.
• Visionary mindset — thrives in ambiguity, constantly pushes for 10x improvements, and wants to help shape how AI redefines GTM.
• Nice to haves:
• Running POVs, pilots, or implementations with enterprise prospects.
• Working directly with AEs during live sales cycles.
• Partnering with technical teams (Forward Deployed Engineers, Product, or Data) on integrations, model training, or workflow design.
• Building scalable GTM systems (Clay, enrichment waterfalls, outbound automation).

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.