Sales Representative

Pay: Up to $200,000.00 per year

POSITION SUMMARY

You will be the first point of contact for anxious, concerned, and highly invested parents who are seeking guidance during one of the most critical decisions of their child’s life, their future.

As a Sales Representative at Kate Stone Prep , you’ll play a key role in driving business growth by connecting with prospective clients, nurturing warm leads, and generating new opportunities. Your ability to build immediate trust, communicate with warmth and professionalism, and clearly articulate our value will be essential to your success.

In this role, you’ll manage both inbound and outbound sales calls, follow up with leads, and proactively prospect to expand our client base. You’ll also collaborate closely with our marketing team to improve conversion rates and close high-quality clients.

You must be confident and polished in a variety of settings, whether that’s speaking on camera, presenting in front of a packed room of parents, or building rapport through one-on-one conversations. We’re looking for a refined communicator , someone who puts families at ease, asks thoughtful questions, and makes parents feel both heard and supported.

This role is perfect for someone who loves building trust through conversation, is motivated by performance and income potential, and wants to grow with a company that’s redefining what it means to prepare young people, not just for college, but for life.

We offer ongoing training, mentorship, and a significant opportunity for growth as we scale rapidly.

Join us in transforming the college admissions journey, and solving the education crisis, one family at a time.

ABOUT THE COMPANY

At Kate Stone Prep, we build wildly successful lives for our students through education, mentorship, and powerful connections. The core problem we solve for families is helping their children gain admission to top-choice colleges and careers. Our approach is different. We don’t check boxes, we break the outdated college coaching models. While most candidates start to look the same on paper, our students complete inventive, one-of-a-kind projects that stretch their potential, tell a compelling story, and position them as unmistakably competitive.

Working with us means joining a team that is deeply devoted to the mission. We’re building something exceptional, a new standard of educational mentorship that high-achieving families instantly recognize as different. This role isn’t about rattling off features; it’s about earning trust by asking the right questions, speaking with clarity and calm confidence, and helping families see what’s possible for their child. Our clients are discerning. They’re looking for someone who understands their values, respects their time, and can guide them toward the right decision without pressure. Our most successful sales reps are poised, well dressed, emotionally intelligent, and take pride in delivering a concierge-level experience. They show up to weekend workshops not just because that’s when families are available, but because they know that’s when the most meaningful conversations, and biggest opportunities, happen. If you’re driven to grow your income, your influence, and your role in a fast-scaling company, we’d love to meet you.

OBJECTIVES

• Respond to Inbound Leads with Urgency + Warmth: Be the first point of contact for families reaching out through phone calls, website inquiries, and marketing-driven leads. Represent the brand with professionalism, care, and clarity, creating immediate trust from the very first interaction.
• Build Strategic Relationships: Proactively connect with high-intent families through referrals, community networking, and in-person events. Represent our mission with poise and authenticity while building lasting relationships.
• Conduct Deep Discovery: Listen closely to understand each family’s goals, values, and concerns. Offer thoughtful, tailored recommendations to help them make the most informed decision.
• Communicate with Clarity + Confidence: Present our services in a way that speaks to outcomes, transformation, and long-term impact, rather than features. Help families envision what's possible for their child.
• Manage & Nurture the Sales Pipeline: Use Hubspot to track activity, stay in sync with follow-ups, and move families through the enrollment process with consistency and ease.
• Follow Up with Intention: Create timely, meaningful touchpoints across multiple channels, phone, email, text, video, handwritten mail, in-person, and event-based outreach, to deepen trust and move the conversation forward.
• Close with Integrity: Address objections with care, provide clear answers, and help families move forward with confidence, turning high-quality leads into lifelong clients.
• Exceed Growth Goals: Consistently meet or surpass monthly and quarterly sales targets through personalized outreach and strategic engagement.
• Deliver White-Glove Service: Ensure every touchpoint reflects the high standards of Kate Stone Prep, from first inquiry to enrollment, leaving families feeling seen, supported, and confident.
• Collaborate Cross-Functionally: Work in partnership with the marketing, operations, and coaching teams to align messaging and create a seamless client experience.
• Track Key Metrics: Maintain up-to-date records of activity and performance using Hubspot. Monitor lead progress and provide reporting on sales trends and outcomes.
• Stay Informed: Keep up with trends in college admissions, competitive offerings, and family expectations to remain a trusted expert.
• Invest in Growth: Participate in team trainings, mentorship, and ongoing learning to continuously improve your communication, performance, and leadership potential.

COMPETENCIES

• Sales Discovery Mastery Able to lead high-stakes discovery calls with confidence and structure, asking thoughtful questions, identifying pain points, and guiding families toward clarity.
• High-Touch Relationship Management Skilled in building and nurturing trust with prospective clients through consistent, personalized follow-up across multiple channels (calls, emails, texts, in-person, etc.).
• Persuasive Communication Delivers clear, confident messaging in high-pressure moments, on stage, on camera, and one-on-one, with a polished, composed presence.
• Strategic Objection Handling Responds to objections with empathy and insight, reframing concerns and guiding families to decisions that align with their long-term goals.
• CRM + Sales Pipeline Proficiency Uses Hubspot (or equivalent) to accurately track activity, move leads through the pipeline, and maintain clear, organized records.
• Event-Based Selling Comfortable engaging with families at live events, proactively starting conversations, qualifying interest, and setting up next steps.
• Time + Workflow Management Manages priorities with discipline, balancing outreach, follow-up, event participation, and admin without dropping the ball.
• Cross-Functional Collaboration Works seamlessly with marketing, operations, and coaching teams to align messaging, improve handoffs, and elevate the client experience.
• Outcome-Oriented Messaging Frames service offerings around transformation and value, not features, anchoring the conversation in outcomes, impact, and return on investment.
• Adaptive Selling Strategy Adjusts approach based on audience, emotional context, and decision dynamics, demonstrating emotional intelligence and composure under pressure.

BENEFITS

• $45,000 base salary + performance-based commission
• Opportunity to earn $65K–$195K+ annually
• Health insurance coverage available after 90 days of employment

LOCATION & SCHEDULE

This is an in-person position based out of our Darien, CT office. Regular business hours apply, with flexibility for evening or weekend events as needed to support families and team growth.

EDUCATION AND EXPERIENCE

• High School Diploma or GED (Required)
• 3-5 Years of High Ticket sales experience (Required)

PHYSICAL REQUIREMENTS

• Ability to Sit or Stand for Extended Periods : Comfortable working at a desk, making outbound calls, and engaging with clients via phone, email, or video calls for extended hours.
• Manual Dexterity : Ability to type, use a computer, and handle office equipment (e.g., phone, keyboard, mouse) with ease.
• Light Lifting : Occasionally may need to lift office supplies or equipment up to 10-15 pounds (e.g., boxes, marketing materials).

COMMITMENT TO DIVERSITY

As an equal opportunity employer committed to meeting the needs of a multigenerational and multicultural workforce, Kate Stone Prep recognizes that a diverse staff, reflective of our community, is an integral and welcome part of a successful and ethical business. We hire local talent at all levels regardless of race, color, religion, age, national origin, gender, sexual orientation or disability, and actively foster inclusion in all forms both within our company and across interactions with clients, candidates and partners.

If this position caught your eye, send us your resume! For best consideration, include the job title and source where you found this position in the subject line of your email to View email address on click.appcast.io . Already a candidate? Please connect directly with your recruiter to discuss this opportunity.

Job Type: Full-time

Compensation Package: Commission pay

Work Location: In person