Summary
Overview
Work History
Education
Skills
Timeline
Generic

Dylan Sipler

Boca Raton

Summary

Results-driven SMB Account Executive with 4 years of experience in sales and 2 years in B2B SaaS sales, consistently exceeding $500k ARR quotas through creative outreach and consultative selling. Proven track record of engaging a wide range of prospects, uncovering complex business needs, and delivering tailored bookkeeping and accounting solutions that streamline backend business operations. Adept at leading discovery, orchestrating high-impact product demos to ensure revenue generation. Highly proficient in Salesforce pipeline management, with a strong ability to build relationships, influence decision-making, and drive scalable growth in fast-paced, high-performance environments. Seeking to bring a revenue-generating mindset and platform fluency to accelerate expansion in the enterprise market.

Overview

4
4
years of professional experience

Work History

Senior Account Executive

Finally.com
10.2023 - Current
  • Surpassed FY2024 quota by 150%, consistently exceeding targets and driving revenue growth.
  • Closed $758,196 in new ARR across 174 SMB accounts, showcasing high-volume deal execution and versatility across multiple verticals including healthcare, professional services, construction, SaaS, non-profits, and hospitality/F&B.
  • Recognized as the top-performing Account Executive of 2024, leading the team in revenue
  • Maintained top sales performance with $354,648 in ARR generated by April 2025, reinforcing position as a team leader in revenue generation.
  • Led discovery across a diverse range of businesses to uncover bookkeeping, accounting, and expense management needs; presented solution-driven demos of the Finally Platform tailored to prospect pain points, and structured pricing to create urgency while maximizing profitability and ensuring deal closure.
  • Implemented a Trustpilot review strategy that drove the highest volume of 5-star reviews across the sales team, strengthening brand credibility, boosting deal closure, and enhancing overall customer trust.
  • Utilized Salesforce to manage pipeline, track deal progress, and maintain accurate forecasting.

Account Executive

NewDay USA
08.2021 - 08.2023
  • Identified clients’ financial needs across debt consolidation and asset management, presenting tailored loan solutions to optimize financial outcomes.
  • Closed $14.4M in funded loan volume across 60 clients by August 2023, consistently surpassing performance benchmarks.
  • Negotiated favorable deal structures, incorporating closing costs that increased company profit margins by integrating 4% of the loan amount into funded deals.
  • Averaged a 23-day loan cycle from open to close, outperforming the company average of 35 days through strong communication and time management.
  • Built lasting client relationships that resulted in high satisfaction and numerous 5-star reviews on Trustpilot, reinforcing company reputation and referral business.

Education

Bachelor of Science - Crime And Criminology

James Madison University
Harrisonburg, VA
05-2021

Skills

  • Lead qualification
  • Consultative sales
  • Strategic discovery and pain-point mapping
  • Strategic planning
  • Relationship building
  • Objection handling
  • Product demoing
  • Deal structuring
  • Negotiation
  • Closing
  • Sales quota achievement

Timeline

Senior Account Executive

Finally.com
10.2023 - Current

Account Executive

NewDay USA
08.2021 - 08.2023

Bachelor of Science - Crime And Criminology

James Madison University

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