Jordan Bickerton

Sales Development Representative II at Hyland

Greater Cleveland

About

Hard-working and results-driven SaaS sales professional with a proven track record of exceeding revenue targets and driving meaningful business impact. Currently excelling as a Sales Development Representative II at Hyland, I focus on strategic outreach, building client relationships, and contributing to the success of the Financial Services & Insurance vertical. This year has been one of real growth — both in results and in the depth of my understanding of how organizations can leverage automation, AI, and content solutions to solve real business challenges. I’ve consistently exceeded quota — 114% in Q2, 115% in Q3, and pacing above 125% for Q4 — through thoughtful, targeted outreach and close collaboration with my teammates. The most rewarding part has been seeing that work translate into measurable impact: creating quality opportunities, driving pipeline, and delivering messaging that resonates. Throughout my career, I’ve consistently ranked among the top performers in competitive SaaS sales environments. Prior to Hyland, I ranked in the top 3% of a 75-person SDR team at Seamless.AI, averaging 156% of quota attainment, mentoring fellow reps, and helping to drive team performance and culture. I’m passionate about driving pipeline growth, developing strategic outreach initiatives, and creating lasting client relationships that fuel organizational success.

Experience

  • Sales/Business Development Representative II at Hyland
    Mar 2025 - Present · 1 yr 5 mos

  • Personal Trainer & Nutrition Coach at JB Consulting Group, LLC
    Jan 2023 - Present · 3 yrs 7 mos

    - Generate transformative results from weight loss, body recomposition, and muscle gain, and address hormonal health through proper nutrition. - Weekly 1:1 check-ins to hold clients accountable and address any concerns as well as instilling confidence in progression. - Customize training and nutrition programs providing personalized solutions tailored to clients’ overall health and fitness goals. - Proactively monitor client progress, adjusting training programs as needed to address individual challenges and optimize outcomes. - Build long-lasting relationships with clients through authentic interaction and communication. Instruct 27 clients both in-person and online through my own business. - Extensive knowledge with the kinesthetics, joint functions, muscular movements, and performance of the human body through hands-on experience. - Generate referrals through testimonials of current clients and word-of-mouth. - Manage appointments and client records to ensure an organized training experience with an upward trajectory.

  • Sales Development Representative at Seamless.AI
    Sep 2024 - Feb 2025 · 6 mos

    - Consistently ranked in the top 3% of a 75-person outbound SDR team every month. - Contribute significantly to team success and company growth by driving revenue and exceeding targets consistently. - Achieve 156% of quota during the first month in training, 210% of quota in the second month, leading the team in held meetings; 119%, 133%, and consistently over quota in subsequent months. Quota being 1.5 meetings held per day worked, an average of 30 held meeting per month. - Generate over $50K in ARR within five months from completed sales cycles. - Exceeding booked-to-held meeting ratio month after month with 90%, 86%, 80%, and consistently over the minimum 65% in subsequent months. - Regularly address the outbound team of 75 reps, presenting results and sharing insights. - Identify individual strengths and areas for growth within the team, delivering tailored feedback to enhance performance. - Taking the initiative to conduct weekly discussions on mindset and success strategies as an SDR. - Instilling confidence in team members by regularly reinforcing their strengths, recognizing achievements, and aligning their efforts with growth opportunities. - Sole SDR invited to speak at the company’s Q3 All Hands meeting, selected by the VP of Inside Sales. - Experience with Salesforce CRM, SalesLoft, Koncert Dialer, LinkedIn Sales Navigator, Hyperbound, and Lattice. - Familiarity with all B2B Lead Generation tools ZoomInfo, Apollo.io, Lusha, LeadIQ, 6Sense, etc.

  • Life & Health Insurance Broker at Insurance Elevated
    Jan 2024 - Jan 2025 · 1 yr 1 mo

    - Managed end-to-end sales cycles, from outbound prospecting to finalizing agreements. - Safeguarded financial futures through the sales and planning of variable life insurance policies – 25 customers monthly - Represented major insurance carriers as an agent for Cigna Healthcare, Aetna, Oscar-Stride Health, Molina Healthcare, Mutual of Omaha, Americo, F&G, Ethos, Surebridge, and Transamerica. - Licensed in 11 states to sell life and health insurance. - Prospected daily to expand my network of clientele and followed up on warm leads. - Negotiated and closed deals through explanations of products and their benefits to customers. - Utilized Customer Relationship Management (CRM) software to communicate with and manage clientele.

  • Life Insurance Agent Assistant at American Income Life: AO
    Oct 2022 - Mar 2023 · 6 mos

    - Assisted with closings and maintenance of sales leads on multi-million-dollar accounts. - Developed business proposals and summary sheets for new and current accounts. - Managed agents’ MODS and assisted underwriting in the approval process. - Contacted clients to schedule appointments for policy improvements.