Head of Sales

Head of Sales, Wonsulting

Apply

Complete the Head of Sales application form: https://forms.gle/fybux571JARPW3tG7

Location

Remote within the United States Expected hours: Full time - contract (30 days) to hire Interview timing: As soon as possible

Wonsulting helps people understand where they are stuck in their job search and identify the next step in their career. We are looking for a Head of Sales to grow Services revenue by helping job seekers choose the services that fit their needs and move them forward.

You will own the entire Services sales funnel and lead a talented team of sales reps. This role combines hands-on coaching, pipeline management, data and AI analysis, and close work with operations, customer experience, marketing, product, and engineering.

Responsibilities

Revenue & Pipeline Ownership

• Own Services sales revenue and the full funnel, from lead capture and qualification through booking, discovery, close, and handoff. Lead sales across inbound, outbound, group calls, workshops, and webinars.
• Build a reliable pipeline system with visibility at every stage. Track each lead’s stage, potential sale value, likelihood to convert, expected revenue value, owner, and next action. Use data by source, stage, and rep to diagnose bottlenecks, prioritize opportunities, and give leadership a credible forecast and weekly view of revenue, risks, and actions.

Team Leadership & AI Coaching

• Lead and develop a talented sales team. Use clear goals, one-to-ones, team call reviews, role-play, and rep scorecards to improve discovery, objection handling, service knowledge, and closing.
• Listen to sales calls and use AI to analyze transcripts, identify customer needs and objections, and find patterns in wins and losses. Validate findings against real calls and turn them into specific coaching and better sales playbooks.

Attendance, Conversion & Lead Follow-up

• Increase booking-to-attendance and attendance-to-sale conversion. Improve lead routing, prompt callbacks, calendar confirmation, reminders, rescheduling, and no-show recovery with sales support and operations.
• Build disciplined follow-up for hot and warm leads. Refine lead scoring around service fit, intent, urgency, and engagement; personalize outreach; and make each opportunity’s owner and next step clear.

Advise on Lead Generation & Sales Experimentation

• Work closely with marketing, product, and engineering to grow lead volume and quality. Return clear customer patterns and feedback, with relevant call examples, to improve messaging, booking journeys, and the customer experience.
• Develop promotional strategies and improve outbound, webinar, workshop, and group-call sales motions with marketing. Test scripts, offers, event formats, and follow-up; measure their effect on revenue, conversion, and customer fit.

Sales Operations, Handoffs & Customer Trust

• Own CRM hygiene in ActiveCampaign, including stages, tags, notes, lead scores, ownership, follow-up tasks, and reporting. Work with operations and engineering to resolve gaps in tracking and automation.
• Take ownership of active opportunities, reporting, and SOPs during onboarding. Keep playbooks current and ensure a clear sales-to-delivery handoff, with customer goals, agreed services, and expectations documented.
• Protect sales quality and customer trust. Coach accurate service explanations, appropriate recommendations, and ethical selling; partner with service delivery and customer experience to address recurring expectation gaps.

What We Are Looking For

• At least 8 years of experience in high-ticket sales roles, with demonstrated success owning a sales funnel and improving revenue, show rates, or conversion.
• At least 4 years of experience managing a sales team, including coaching reps through call reviews, practical feedback, role-play, and performance scorecards.
• Strong analytical judgment: you can work with imperfect funnel data, build credible forecasts, and turn findings into clear priorities and measurable experiments.
• Hands-on experience with CRM pipelines, lead scoring, follow-up workflows, and reporting. You can make sales data reliable enough to guide decisions.
• Ability to use AI for ops, transcript analysis and rep coaching, check its conclusions against source material, and handle customer information responsibly.
• Bonus points: Sales experience in a services or coaching business.

What Success Looks Like

Your primary measure of success is Services revenue growth.

The leading indicator is a reliable pipeline system: at any point, you can see each lead’s stage, potential sale value, likelihood to convert, expected revenue value, owner, and next action. You can explain what each stage of the pipeline is worth, where leads are progressing or stuck, and which actions will improve the revenue forecast and move qualified leads forward.

Revenue growth should come from helping people understand where they are stuck in their job search, identify the next step in their career, and choose services that fit their needs.

Apply

Complete the Head of Sales application form: https://forms.gle/fybux571JARPW3tG7 Interviews will begin as soon as possible.

Work Location: Remote