Karyn Ross
Summary
Versatile and results-driven professional with extensive experience in sales and client management within the tech sector, specializing in strategic planning, customer engagement, and cross-functional collaboration. Proven track record of consistently exceeding revenue targets and leading high-performing teams, underpinned by deep expertise in market analysis, go-to-market strategy, and customer-centric messaging. Adept at leveraging frontline sales insights to develop compelling product positioning and go-to-market messaging that resonate with target audiences. Skilled in creating impactful sales enablement content and coaching teams to drive revenue acceleration, market growth, and sustained competitive advantage.
Overview
20
20
years of professional experience
1
1
Certification
Work History
Manager Strategic Initiatives
Teaching Strategies
Washington, D.C.
08.2024 - Current
- Lead and scale SDR and cross-sell teams by recruiting, training, mentoring, and coaching team members to consistently exceed performance targets.
- Rebuild and optimize SDR and cross-sell functions, significantly increasing pipeline contribution and overall team performance.
- Develop and implement scalable go-to-market outreach strategies across phone, email, and social channels to drive engagement and demand generation.
- Oversee pipeline generation to ensure alignment with sales objectives and direct contribution to sustained pipeline growth.
- Establish and monitor key performance indicators (KPIs), using data insights to drive continuous improvement in productivity and effectiveness.
- Collaborate cross-functionally with Sales, Marketing, and Revenue Operations to align messaging, improve lead quality, and streamline handoff processes.
- Standardize sales playbooks, cadences, and outreach scripts to ensure consistent messaging and scalable team growth.
- Leverage tools such as Salesforce, SalesLoft, and Outreach to enhance performance, improve efficiency, and enable data-driven decision-making.
- Develop talent into high-performing sales professionals through hands-on coaching and ongoing mentorship.
- Increase annual recurring revenue (ARR) by driving net-new customer acquisition and expanding B2B market presence through targeted outbound strategies and optimized sales development efforts.
- Thrive in fast-paced, high-growth environments with proven expertise in scaling outbound sales programs and refining go-to-market strategies.
Senior Account Executive
Teaching Strategies
Washington, D.C,
04.2021 - 08.2024
- Led go-to-market strategies targeting the Education sector, including RFP development and tailored messaging, resulting in new B2B business acquisition in a highly competitive market.
- Positioned and promoted assessment solutions by aligning product capabilities with customer needs, enhancing market penetration and strengthening brand positioning.
- Oversaw the integration of learning technologies, ensuring seamless onboarding, product adoption, and customer success—key drivers of retention and loyalty marketing.
- Developed and executed customer journey strategies, including onboarding programs and ongoing health checks, to boost engagement, satisfaction, long-term loyalty, and upsell potential.
- Collaborated cross-functionally with Sales, Product, and Operations to create detailed customer profiles and personas, driving targeted campaigns and outreach strategies.
- Implemented and optimized a CRM system to enhance lead tracking, campaign performance reporting, and sales forecasting—empowering data-driven marketing decisions.
- Analyzed KPIs and customer engagement metrics to refine messaging, improve campaign performance, and support upsell and cross-sell initiatives.
- Delivered presentations at internal sales and marketing trainings to align on brand messaging, share buyer behavior insights, and promote best practices in customer engagement.
- Played a key role in securing and expanding high-value accounts, contributing to both near-term revenue growth and long-term brand expansion.
- Consistently exceeded sales and engagement goals by applying customer-focused strategies and leveraging insights to drive acquisition, conversion, and retention.
Account Executive | EdTech Lesson Editor
Legends of Learning
Remote
05.2019 - 04.2021
- Created, curated, and optimized K–5 EdTech classroom math games to support program onboarding and improve student learning outcomes.
- Played a key role in increasing customer retention by 20% through the enhancement and delivery of engaging, results-driven product training sessions.
- Managed client accounts with a focus on relationship building, ensuring satisfaction, renewal, and long-term engagement with EdTech solutions.
- Facilitated successful contract negotiations, securing new deals and strengthening client partnerships to support business growth and retention objectives.
K-12 School Counselor
Feynmen School
Bethesda, MD
08.2018 - 05.2019
- Applied diverse instructional strategies to support students' physical, emotional, social, and intellectual development, fostering a holistic and inclusive learning environment.
- Collaborated with colleagues and school leadership to develop, evaluate, and enhance curriculum, ensuring alignment with academic standards and student needs.
- Established partnerships with local organizations to provide additional resources and support for at-risk and underserved students.
- Facilitated IEP and 504 meetings to ensure appropriate accommodations, advocate for student needs, and align individualized plans with instructional goals.
K-12 School Counselor
St. Ann School School
West Palm Beach, FL
08.2005 - 07.2009
- Coordinated peer mentoring programs that encouraged positive relationships between older and younger students.
- Enhanced students'' social and emotional well-being by implementing comprehensive counseling programs.
- Established productive relationships with community partners to expand available resources for student success.
- Supported families during times of transition or crisis by connecting them with appropriate community resources.
- Implemented evidence-based practices within the counseling program, ensuring effectiveness and alignment with professional standards.
- Promoted diversity and inclusion by organizing culturally-responsive events, fostering an understanding of diverse perspectives among students.
Education
Master of Arts - Psychology
The George Washington University
Washington, D.C. Masters of Education - Counseling
The George Washington University
Washington, D.C. Skills
- Strategic Planning
- Business growth strategy
- Client engagement strategies
- Market growth strategies
- Market entry strategy
- Sales Forecasting
- Contract Negotiation
- Effective team leadership
- Proficient in CRM software
- Asana project management
- Development of sales teams
- Field marketing execution
- Long-term strategic planning
- Proficient in change management
Accomplishments
- 2025 Company First Award
- 2022 Account Executive of th Year
Certification
- Project Management Coursework
- Change Management Coursework
Timeline
Manager Strategic Initiatives
Teaching Strategies
08.2024 - Current
Senior Account Executive
Teaching Strategies
04.2021 - 08.2024
Account Executive | EdTech Lesson Editor
Legends of Learning
05.2019 - 04.2021
K-12 School Counselor
Feynmen School
08.2018 - 05.2019
K-12 School Counselor
St. Ann School School
08.2005 - 07.2009
Master of Arts - Psychology
The George Washington University
Masters of Education - Counseling
The George Washington University