Vice President of Sales

• MyTime has product-market fit. Our platform is mature, differentiated and proven at enterprise scale, and the business has already scaled into the double-digit millions in revenue — largely on the strength of the product and word of mouth
• We are now making a deliberate investment in a dedicated enterprise sales motion, and hiring the leader who will architect it
• You will be designing that motion, not inheriting one. The playbook, the team, the named-account model, the forecast — all of it is yours to build
• You will close anchor enterprise accounts personally, turn how you won them into something repeatable, hire the account executives who run it, and coach them until they can do it without you. In year one, you build and sell
• As the team scales, your job shifts from personally proving the motion to building the organization that executes it. In year two, you are running the engine that defines how this company grows
• These are real enterprise deals — multi-location and franchise brands, complex buying committees, and sales cycles measured in quarters and sometimes longer. When you win one, you win dozens or hundreds of locations at once
• Personally closing anchor enterprise accounts
• Building a predictable enterprise pipeline engine — named-account prospecting, executive outreach, inbound conversion, and partner and referral channels
• Building the playbook — discovery, business case, committee navigation, competitive displacement
• Standing up the operating system: stage definitions, qualification criteria, pipeline instrumentation, forecasting, named-account planning, quotas and compensation design
• Hiring, ramping and coaching the account executive team
• Running a forecast with enough discipline and integrity that the CEO and board can actually plan against it
• What success looks like in your first year:
• Closed enterprise logos, with the winning patterns codified into the playbook
• A sales methodology that is documented, taught, and demonstrably repeatable
• Qualified pipeline built to a coverage level that supports the following year’s plan
• A forecast that holds up against actuals, consistently
• Your first account executives hired, ramped and certified against a clear performance bar
• Evidence that reps other than you can win with the motion you built

Benefits

• Health, dental, and vision insurance
• 401(k) plan
• Generous vacation policy and paid holidays
• Remote-first company
• Opportunity for professional growth and development
• Dynamic work environment

• You have sold to, or worked in, multi-location or franchise businesses
• 8+ years in enterprise SaaS sales, including 4+ years leading teams — with the willingness to carry a personal number during the build phase
• You have sold against an entrenched incumbent where migration risk was the objection that killed deals
• You have designed stage definitions, forecast models, named-account plans and compensation plans yourself
• Product-fluent enough to lead discovery and compelling product demonstrations independently, while knowing when to bring in technical or product expertise
• You have built part of a sales function from scratch: first playbook, first hires, first instrumentation
• A demonstrated record personally closing six-figure enterprise SaaS deals through complex, multi-stakeholder buying processes and extended sales cycles
• 10+ years of sales experience, preferably in scaling a metrics-driven SaaS sales team at a rapidly growing technology company in a highly competitive market
• High levels of analytical horsepower and ability to turn analysis into insight and actions
• Bachelor’s degree in Business, Sales, Marketing, or related discipline, or equivalent additional experience
• Preference for experience selling into Multi-Location or Franchises but any industry works as long as sale was $250 K+ ACV and involved a complex DMU of 3+ people
• Strong experience using CRM and Marketing Automation tools such as Salesforce, Hubspot, etc
• 3-10 years of sales leadership: hired at least 6 successful, high performing sales reps and managed at least 8 sales reps or managers-of-managers within dynamic sales teams
• Extensive sales operations experience (forecasting, planning, analysis, sales systems, reporting, compensation and quota management)
• Strong problem solving skills, project management, time management
• Very organized with attention to detail
• Executed a sales playbook used to acquire customers with $250K+ ACV. Strong preference for experience in designing and implementing the playbook from scratch. MEDDIC preferred
• Ability to build vision, understand and define requirements, design practical solutions, develop supporting business cases and implement solutions for clients
• Preference for Sales management experience with an organization that has scaled at least to $30+M ARR. Front-office software (i.e. martech, sales-tech, etc.) preferred but will accept any complex software sales except ad sales or hardware
• Preferred: vertical SaaS for physical-location service businesses — beauty, wellness, fitness, pet care, home services, restaurant, dental, veterinary or automotive. Franchise fluency: advisory councils, master agreements, royalty structures