A core part of this role is using AI to close the gap between "we know what reps should be doing differently" and "reps are actually doing it." You'll be expected to identify specific productivity and skill gaps from call, pipeline, and performance data, then design AI-powered workflows — not just AI-assisted content — that put the right nudge, prompt, or resource in front of the right rep at the right moment in their selling motion. This is a build-and-operate mandate, not a research project: you're expected to ship workflows that measurably change rep behavior.
In addition, you will lead enablement initiatives including but not limited to: new product launches, pricing and packaging rollouts, everboarding programs, skills development, and process adoption. You won't just deliver training — you'll design scalable systems that improve execution quality, shorten sales cycles, increase win rates, and elevate seller confidence.
This is a highly cross-functional, high-visibility role for someone who thrives in fast-moving environments, doesn’t let things slip through the cracks even though they are juggling multiple initiatives at once, knows how to influence senior stakeholders which includes our CEO, and can connect enablement efforts directly to business outcomes.
Responsibilities Include:
Diagnose Gaps & Design AI-Powered Rep Workflows
Mine call recordings, CRM data, pipeline metrics, and win/loss trends to pinpoint specific productivity gaps by rep, segment, or stage (e.g., weak discovery on a given package, slow follow-up after demo, inconsistent qualification)
Translate identified gaps into AI-powered workflows that intervene at the point of work — e.g., real-time call prompts, auto-generated next-best-action nudges, AI-drafted follow-up emails tailored to deal stage, or automated coaching flags routed to managers
Own the full loop: gap identification → workflow design → rollout → adoption measurement → iteration, so workflows keep pace with what the data is showing
Prioritize which gaps are worth building an AI workflow for vs. addressing through traditional training, based on rep time saved and expected impact on productivity metrics (activity volume, cycle time, win rate)
Product Enablement: Lead end-to-end enablement strategy for new product, pricing, and positioning launches — partnering with Product Marketing to translate messaging into talk tracks, demo flows, competitive positioning, and launch certification programs with measurable adoption metrics (call behaviors, pipeline mix, win rate impact)
Skills & Everboarding Enablement: Design ongoing AE development programs across core selling motions, operationalizing skills frameworks (e.g., MEDDPICC) into repeatable training with structured learning journeys tied to tenure and performance
Leadership Enablement: Build and deliver manager playbooks and coaching tools — for both first-time and tenured frontline managers — to inspect call quality, qualification depth, and deal strategy, supporting coaching cadences that drive measurable lift in win rates
Use AI tools (e.g., Gong AI, Claude, Notion AI, or similar) to accelerate production of talk tracks, battlecards, and certification content, and keep it current as messaging evolves
Define success metrics for every initiative, tracking leading indicators (behavior change, certification completion, call quality) and lagging indicators (win rate, ACV, ramp time)
Quantify the productivity lift from each AI-powered workflow (time saved per rep, activity or output increase, downstream effect on pipeline/win rate) and use that data to decide what scales
Serve as a trusted advisor to Sales leadership, aligning enablement priorities to revenue goals and presenting impact insights to executives
Act as the internal champion for AI-driven productivity gains across the Revenue org — helping reps and managers adopt the workflows you build, not just the tools themselves
Drive Key Enablement Initiatives
Measure Impact & Partner Strategically
Within 30 days you'll...
- Complete ChowNow New Hire Onboarding Experience
- Build strong relationships with Sales leadership, frontline managers, Product, Marketing, and RevOps
- Audit existing AE enablement programs, onboarding, assets, certifications, and tooling
- Review pipeline metrics, win/loss data, and call recordings to identify execution gaps
- Identify top 3 performance levers impacting AE productivity — and flag which ones are candidates for an AI-powered workflow vs. traditional enablement
- Get up to speed on ChowNow's current AI and call-intelligence tooling (e.g., Gong AI) and what's already been tried
Within 60 days you'll...
- Roll out and measure at least one high-impact enablement initiative identified
- Design and launch new AI-powered workflows targeting a specific identified gaps (e.g., an automated coaching flag, a next-best-action prompt, an AI-assisted follow-up workflow) and begin tracking the impact on rep productivity
- Establish an ongoing AE everboarding calendar tied to performance data
- Present early progress and insights to Sales leadership
Within 90 days you'll...
- Achieve defined adoption metrics for at least one major initiative
- Show a measurable productivity result from at least one AI-powered workflow (e.g., time saved per rep, increased activity, improved conversion at the targeted stage) and a plan to expand or retire it based on the data
- Demonstrate early indicators of revenue impact (improved discovery quality, improved pipeline hygiene, increased attach rate, etc.)
- Finalize and socialize a 6–12 month AE enablement strategy that includes a pipeline of future AI-powered workflows tied to ongoing gap analysis
You Should Apply If You Have:
- 6+ years of experience in Sales Enablement, Revenue Enablement, or Sales Performance roles supporting Account Executives or Account Managers in a SaaS or high-growth technology environment
- A proven track record leading enablement programming lifecycles end to end
- Deep understanding of SaaS sales cycles (especially SMB)
- Demonstrated experience turning a diagnosed performance gap into an AI-powered workflow or tool that changed rep behavior at scale — not just using AI to draft content, but designing a system reps interact with in their day-to-day work
- Comfort working hands-on with AI/automation tools (e.g., Gong AI, generative AI platforms, workflow automation tools) to prototype and ship these workflows without heavy engineering support
- Experience operationalizing discovery and value frameworks into scalable programs (BANT, MEDDPICC, etc)
- Strong data fluency — ability to tie enablement initiatives to measurable business impact (win rate, ACV, pipeline conversion, ramp time, etc.)
- Experience partnering closely with Sales, Product Marketing, RevOps, and frontline Sales Managers
- Experience supporting call coaching platforms (Gong) and embedding coaching frameworks into manager rhythms
- Excellent executive communication skills; comfortable presenting to senior leadership
- Strong organization skills and can lead multiple concurrent initiatives without losing quality or velocity
About Our Benefits:
- Estimated Base Salary: $130,000- $172,000 (depending on candidate location and experience)
- Ongoing training and growth opportunities.
- A "Best Place to Work" winner multiple times where we focus on creating a great employee experience.
- Rock solid medical, dental, and vision plans.
- Mental Health Coverage - we offer several programs to support your mental health and wellness goals.
- Unlimited Paid Vacation. We expect you to work hard, but still enjoy your personal life
- 7 weeks of baby bonding time for all new parents (within the first year of birth or adoption), 8 Weeks of Paid Pregnancy Leave.
- 401(k) Matching
- Employer-contributing student loan assistance program or continuing education reimbursement program
- Employee Stock Incentive Plan.
- Pet insurance for your fur babies
- Consistent & fair leadership: we’ll share info, set clear goals, show you respect, and treat everyone fairly.
- Enough freedom to spread your wings while still holding you accountable.
Skills Required
- 6+ years of experience in Sales Enablement, Revenue Enablement, or Sales Performance roles supporting Account Executives or Account Managers in a SaaS or high-growth technology environment
- Proven track record leading enablement programming lifecycles end to end
- Deep understanding of SaaS sales cycles, especially SMB
- Experience turning a diagnosed performance gap into an AI-powered workflow or tool that changed rep behavior at scale
- Hands-on experience with AI and automation tools, including call intelligence, generative AI, or workflow automation platforms
- Experience operationalizing discovery and value frameworks such as BANT or MEDDPICC
- Strong data fluency and ability to connect enablement initiatives to measurable business impact
- Experience partnering with Sales, Product Marketing, Revenue Operations, and frontline Sales Managers
- Experience supporting call coaching platforms such as Gong and embedding coaching frameworks into manager rhythms
- Excellent executive communication skills and comfort presenting to senior leadership
- Strong organizational skills with the ability to lead multiple concurrent initiatives
What the Team is Saying
ChowNow Compensation & Benefits Highlights
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Healthcare Strength — Health coverage is described as comprehensive, spanning medical, dental, vision, and dedicated mental‑health benefits. Wellness resources such as counseling and EAP-style support are also referenced.
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Leave & Time Off Breadth — Time away is positioned as unlimited paid vacation with paid holidays alongside paid parental and family leave. Public benefit descriptions emphasize generous PTO and flexible time off.
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Parental & Family Support — Parental benefits are portrayed as strong, with baby‑bonding time for all parents plus additional paid pregnancy leave. Adoption assistance and a return‑to‑work program are also noted.
ChowNow Insights
What We Do
ChowNow’s vision is to become the leading North American platform connecting diners and independent restaurants for at-home dining. The ChowNow Platform continues to grow its product offerings and bring restaurants and diners closer together. Our marketplace provides commission-free ordering for restaurants nationwide and diners with an ever-growing selection of independent restaurants. Our demand network provides diners with the ability to order where they’re already online, including Google, Yelp, Instagram, Snap, and many others. And our white-labeled online ordering system provides restaurants with a branded experience for diners on their website and their own iOS and Android apps for a reasonable monthly fee regardless of order volume. To date, we’ve created over 20,000 apps for our restaurant partners – something that’s never been done before in our category. We operate this way because of our belief in being fair, sustainable, and equitable with our restaurant partners and the same goes for our culture.
Why Work With Us
Diversity, teamwork, and mutual respect are among our core company values. We pride ourselves on giving our teams plenty of opportunities to make their mark. Join us and help ensure ChowNow becomes the diner’s first choice for socially responsible online ordering. Together we can preserve neighborhood flavor, one restaurant at a time.
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ChowNow Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy asks local Los Angeles employees to come in 2 times a week to allow for in person collaboration and cross-functional relationship building. Our open air, Culver City Headquarters is spacious and inviting for teams to be together.
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