Senior Manager, Sales Enablement

Numeral is building the automation backbone for SaaS, ecommerce, wholesale and manufacturing — starting with the painful world of sales tax compliance. We handle everything from registration to remittance, delivering a white-glove service so e-commerce businesses can stay laser-focused on what they do best: growing their products, customers, and teams.

We’re one of the fastest-growing companies from Y Combinator’s W23 batch, backed by top-tier investors including Benchmark Capital. Our team has deep roots from the early days at Stripe, Airbnb, Notion, and other breakout companies — and now we’re bringing that same level of craft, speed, and ambition to a space that’s long overdue for reinvention.

Numeral is small but mighty. Growth is already borderline unmanageable — which means every hire we make now will directly shape the trajectory of the company. If you’re excited about joining as an early team member and want the kind of ownership that defines careers, we want to meet you.

Running an online business today means wearing a thousand hats — most of them not the reason founders started their company. Our mission is to eliminate the administrative and accounting burdens that distract businesses from doing what they love.

We’ve already helped hundreds of merchants avoid the headache of building giant finance teams just to manage tax compliance. Tomorrow, we’re scaling that impact even further: building the automation layer that lets internet businesses stay nimble, compliant, and future-proof.

We’re hiring a Senior Manager, Sales Enablement to build and scale a best-in-class enablement function at Numeral.

This role is responsible for driving rep productivity, sales process rigor, messaging consistency, competitive readiness, and enterprise deal excellence across the GTM team. You’ll work cross-functionally with Sales, Product, Marketing, and RevOps to ensure our team has the structure, skills, and systems needed to win consistently.

This is a high-impact builder role — not just running trainings, but architecting the enablement engine that powers predictable revenue growth.

• Own rep productivity, onboarding, and ongoing training programs

• Drive sales methodology, qualification rigor, and pipeline discipline

• Codify messaging, discovery frameworks, and value articulation

• Build competitive enablement (vs. Avalara, Anrok, Vertex)

• Enable pricing and packaging strategy to reinforce value-based selling

• Develop vertical and enterprise playbooks to scale upmarket motion

• Lead product release readiness and cross-functional GTM alignment

• Drive Salesforce, Gong, and Outreach adoption and pipeline hygiene

• Identify performance gaps and build targeted enablement to improve win rates

• Equip managers with coaching frameworks to elevate team performance

• 6+ years in Sales roles (Account Executive, Account Management, etc).

• 3+ years in Sales Enablement, Sales Leadership, or Revenue Operations roles in B2B SaaS

• Experience supporting mid-market and enterprise sales teams

• Strong background in sales methodology and pipeline discipline

• Demonstrated success improving rep productivity and win rates

• Experience building scalable playbooks and enablement programs

• Strong analytical skills; ability to turn deal insights into action

• Excellent cross-functional collaboration skills

• Executive presence and ability to influence senior stakeholders

• Experience in fintech, tax, compliance, or infrastructure software

• Experience scaling enablement at a high-growth startup