Bridget Winston

VP of Sales

PatientNow

vp_salesOutbound HeavyConsultative
Deal Size: $15K-50K ACV
Sales Cycle: 1-3 months
Posted by Bridget Winston

Overview

You run sales at PatientNow, which sells practice management software to aesthetic med spas, dermatology practices, and wellness clinics. You're splitting time between strategic work with the CRO, coaching your team through deals, and jumping into complex opportunities yourself. This is not a pure management role—you'll be in deals weekly, modeling the right behavior and helping close when it matters.


Role Snapshot

AspectDetails
Role TypePlayer-coach VP - 50% leadership, 50% player
Sales MotionLikely balanced with outbound emphasis (aesthetic practices don't typically search for software)
Deal ComplexityConsultative - practice owners are entrepreneurs evaluating ROI, implementation lift
Sales Cycle1-3 months (estimated - practice owners move faster than enterprise but slower than transactional)
Deal Size$15K-50K ACV (estimated based on SMB practice management software)
Team QuotaUnknown - you'll own the team number and likely have personal deals

Company Context

Stage: Unknown funding stage - described as "hyper growth" with "real tailwinds"

Size: Unknown employee count

Growth: Actively hiring, CRO describing momentum in aesthetic/wellness market

Market Position: Operating in practice management software for aesthetics/wellness niche - competing against horizontal EMR/practice management tools and other vertical-specific solutions


GTM Reality

Pipeline Sources:

  • Outbound likely dominant - aesthetic practices are busy running their businesses, not actively shopping for software
  • Some inbound from content/referrals as brand builds
  • Partner channel possible (equipment vendors, distributors to aesthetic market)

Team Structure: You're building or optimizing the structure - likely managing AEs and potentially SDR/BDR team

SE Support: Unknown - may have implementation/solutions team for demos and technical validation


Competitive Landscape

Market: Practice management software is crowded. Vertical solutions (aesthetic-specific) compete with horizontal EMR/PM systems that work across specialties.

Common Objections:

  • "We're already using [competitor] and it works fine"
  • "Migration sounds like a nightmare - we can't afford downtime"
  • "Your price is higher than the generic solution"
  • "I need to talk to my office manager/spouse/partner"

Buyer Psychology: Practice owners are entrepreneurial but risk-averse about operations. They care about: patient experience, staff efficiency, revenue capture (reducing no-shows, automating billing), and not disrupting current operations.


What You'll Actually Do

Time Breakdown

Team Leadership (30%) | Strategic Deals (25%) | Coaching/Ride-alongs (25%) | Systems/Process (20%)

Key Activities

  • Team Management: 1-on-1s with your direct reports (likely 3-6 AEs or sales managers), pipeline reviews, forecast calls. You're accountable for the team hitting their number and explaining misses to the CRO and exec team.
  • Active Selling: You'll carry strategic deals - larger practices, multi-location groups, or deals that are stuck. You're demoing, negotiating, and closing these yourself to hit the team number and model best practices.
  • Live Deal Coaching: Joining AE calls to coach in real-time. Reviewing recordings. Helping reps navigate objections, structure pilots, or navigate complex buying committees. You're teaching your process, not just telling people to "close harder."
  • Building Systems: Creating or refining the sales playbook, call scripts, demo flows, qualification criteria, comp plans. Implementing tools and dashboards that create accountability. You're standardizing what works so the team can scale.
  • Hiring & Ramping: Likely hiring AEs or SDRs. You're interviewing, onboarding, and getting new reps productive. You own how fast they ramp.
  • Cross-functional Work: Weekly syncs with marketing (lead quality, messaging), product (feature requests, competitive gaps), CS (handoff process, churn reasons). You're translating what you're hearing in the market back to the company.

The Honest Reality

What's Hard

  • You own the number: If the team misses, that's on you. You're explaining shortfalls to the CRO and board. The pressure is constant.
  • Context switching: One hour you're thinking strategically about territory design. The next you're jumping into a deal that's going sideways. The next you're resolving a comp dispute. It's mentally exhausting.
  • Inheriting problems: You're walking into an existing team and process. Some reps will resist your changes. Some systems will be broken. You'll spend the first 90 days diagnosing what's actually working vs what people say works.
  • Player-coach tension: You need to close your own deals while coaching others. If you're in deals too much, you're not leading. If you're not in deals, you lose credibility and your team number suffers.
  • Market education: Aesthetic practices may not know they need better software. You're often selling the problem before selling your solution. Long educational cycles drain pipeline velocity.
  • Buyer complexity: Practice owners are busy seeing patients. Getting their attention is hard. Getting them to prioritize a software change over other investments (equipment, marketing, staff) is harder.

What Success Looks Like

  • Team hits or exceeds quota consistently - Q over Q growth in bookings
  • Reps are ramping faster - new hires productive in 60-90 days instead of 6 months
  • Win rate improves - you're losing fewer deals to "no decision" or competitors
  • Pipeline is predictable - your forecast accuracy is 90%+, CRO trusts your numbers
  • You're developing future leaders - your best AEs are ready to manage or take on strategic accounts
  • Retention improves - you're keeping top performers, low performers are managed out quickly

Who You're Selling To

Primary Buyers:

  • Practice owners (MD, DO, NP running aesthetic med spa or dermatology practice)
  • Practice administrators/office managers (influence decisions, manage day-to-day operations)
  • Multi-location group operators (buying for 3-10+ locations)

What They Care About:

  • Revenue capture: Reducing no-shows, automating appointment reminders, capturing payments efficiently
  • Staff efficiency: Reducing time on scheduling, billing, and admin so staff can focus on patients
  • Patient experience: Modern booking, text reminders, easy payment - they're competing on experience
  • Implementation risk: They cannot afford downtime. Migration needs to be smooth or they won't switch.
  • ROI: Does this pay for itself in saved staff time, reduced no-shows, or increased bookings?
  • Compliance: HIPAA, data security - they're handling patient data and need to trust your security

Requirements

  • Built and scaled sales teams in high-growth B2B SaaS - you've lived this movie before
  • Managed managers or led teams of 5-15+ reps - you've hired, coached, and held people accountable at scale
  • Can articulate your sales process and methodology - you know WHY you've won, not just that you won
  • Player-coach mentality - comfortable closing deals yourself while developing others
  • Process-driven - you build systems, dashboards, and accountability structures that create predictability
  • Experience selling to SMB or mid-market - understand buying dynamics of entrepreneur owners, not just enterprise committees
  • Comfortable with ambiguity - this is hyper growth, things will be messy and incomplete
  • Deep customer empathy - you respect that practice owners are time-starved entrepreneurs, not just "prospects"
  • Track record of consistent overperformance - you've hit or exceeded quota in multiple roles/companies