Sales Enablement and Operations Lead

This is a fully remote position, open to applicants in Massachusetts.

📋 Description

• Take charge of the onboarding and training process for new GTM and Forward Deployed hires.

• Develop ramp-up programs for Account Executives (AEs), Business Development Representatives (BDRs), and Forward Deployed team members.

• Create and sustain the sales playbook that includes Ideal Customer Profiles (ICPs), personas, discovery, qualification, objections, competitive positioning, and industry-specific strategies.

• Transform product launches and customer successes into talk tracks, demo flows, case studies, and battlecards.

• Manage CRM data, pipeline stages, necessary fields, deal hygiene, and automation processes.

• Conduct weekly pipeline assessments, forecasting routines, dashboards, and sales metrics analysis.

• Oversee the GTM tool stack, which encompasses CRM, sequencing, call recording, and enrichment tools.

• Collaborate with the GTM Engineer to create AI-enhanced workflows using Claude Code.

• Evaluate call recordings and win/loss data to uncover trends and provide coaching to representatives.

• Relay insights back to the product and marketing teams.

• Assist in territory planning, quota establishment, and the mechanics of compensation plans.

⛳️ Requirements

• Familiarity with sales, enablement, or operations, preferably in the B2B SaaS sector.

• Proven experience in developing an enablement program from scratch.

• Capability to conduct training sessions and compile pipeline reports.

• Skill in refining disorganized data and rectifying flawed processes.

• Ability to clarify complex, technical products for sales representatives and buyers.

• Experience in utilizing AI for automating tasks; creating AI tools is an added advantage.

• Capacity to manage tasks from start to finish without a pre-existing playbook.

• Prior experience in selling to or supporting teams that assist customer support/CX leaders, fintech, healthcare, or other regulated sectors is a plus.

🏝️ Benefits

• Flexible working hours.

• Promotions and performance recognition every six weeks.

• Unlimited access to AI tools with no usage restrictions.

• Opportunities for AI skill development through daily engagement with AI.

• Semi-annual company trips to Hawaii.

• Paid trial period of approximately two days.

• A diverse and inclusive work environment.

• A low-ego, high-trust culture.

• Genuine opportunities to influence the product and the company.

• An informal, respectful recruitment process.