Kaylin Howell
Cleveland,OH
Summary
Strategic and results-driven SaaS & Fintech sales leader with a track record of exceeding revenue targets, leading high-performing teams, and driving operational excellence. Proven ability to scale sales teams by 300%+, execute high-impact outbound strategies, and deliver sustained growth. Passionate about coaching and developing future sales leaders through radical candor, emotional intelligence, and a structured approach to sales methodology. Adept at managing rapid change, optimizing sales processes, and leveraging data to drive decision-making.
My motto: The things that people run from are usually the things that success comes from.
Overview
18
18
years of professional experience
1
1
Certification
Work History
District Sales Manager
Toast
Ohio
07.2023 - Current
- Collaborated closely with other district managers to share best practices, learnings, and drive overall success of the organization and standardize processes.
- Improved team performance by providing regular coaching, training, and mentoring to sales representatives.
- Increased sales revenue by developing and implementing effective sales strategies for the region.
- Exceeded annual sales targets through strategic planning, territory optimization, and customer relationship building.
- Grew YOY sales 34% by consistently meeting and exceeding quotas.
- Streamlined operations by collaborating with cross-functional teams to address challenges and improve processes including being a field ambassador for multiple hiring, sales process, and organizational initiatives.
Senior Manager of New Logo Sales
GoCanvas
US And APAC
10.2022 - 07.2023
- President's Club Achiever '22
- Manage a team of full sales cycle of 30 AEs and 4 team leads who translate business needs into system and process configuration
- Assist team with client meetings, presentations, and negotiations
- Manage the entire sales process from lead generation to closing deals and post-sales follow-up to ensure customer satisfaction and retention
- Continuously stay up-to-date with industry trends, competition, and emerging technologies to stay ahead of the curve
- Effectively communicate sales performance, forecasts, and results to senior leadership
- Assist in the recruiting, staffing and training to grow and maintain a sales team
- Formulate and execute on monthly and quarterly sales plans
- Manage productivity, funnel of opportunities, forecasting, and quality to ensure teams meet established goals and standards
- Create, with marketing and operations leaders, ongoing process improvements, recommendations, and implementation of systems that will make the team more efficient
- Assist in achieving target goals for team and individual representatives by managing programs and campaigns as well as joining sales calls when needed
Senior Manager of Business Development
GoCanvas
US And APAC
05.2022 - 10.2022
- President's Club Achiever '21
- Consistent attainment of pipeline generation targets at 120%+ MoM through inbound and outbound efforts
- ($5m average quarterly goal)
- Lead a remote team of 22 SMB and ENT quota-carrying BDRs and 3 managers, ensuring they met personal and team monthly, quarterly and annual goals
- Provided guidance and instruction on a day-to-day basis to ensure team members understood and executed their responsibilities
- Held regular one-on-one meetings with team members to evaluate progress and discuss professional development
- Oversaw sales pipeline growth from Inbound MQLs and Outbound prospecting through to SQL conversions in the sales pipeline
- Developed best practice operating strategies and provided effective direction to the sales enablement team to help to hire, onboard, train and manage a global BDR team
Business Development Manager
GoCanvas
05.2021 - 05.2022
- Managed, upskilled, and developed 10 BDRs remotely
- Collaborated with Sales and Marketing management to develop and execute sales strategies and initiatives
- Oversaw sales enablement and processes for sales development team
- Developed BDRs into sales-ready candidates for future sales roles (promoting 8 reps within 1 year)
- Motivated individuals and team to exceed objectives through coaching, regular broadcast of results, and creative incentives
- Regularly reported to and met with sales and marketing leadership on team/individual results - lead quantity, quality, conversion, revenue
Business Development Manager
OnStation - Powered by PROJiTECH
12.2018 - 08.2021
- Was an executive team member working closely with the CEO and other team members on major strategic initiatives
- Defined and executed strategies to grow our partnerships, pipeline funnel, data analytics services, and cloud enablement services
- Supported the product team in identifying opportunities, providing vertical solutions, and establishing the go-to-market strategy for different verticals
- Lead and managed the day-to-day sales, marketing, and business development activities while attending and presenting product demonstrations to prospects
- Established and maintained strong relationships with key customer stakeholders and continually sought to capitalize on opportunities that would increase customer satisfaction
- Established and maintained strong relationships with strategic partners
Sales Enablement Specialist (North America)
Signet Jewelers
02.2007 - 09.2018
VIP and Partnership Specialist
PlayhouseSquare
Cleveland, United States
08.2010 - 10.2013
Education
Bachelor's degree -
Kent State University
01.2010
Skills
- HubSpot
- Salesforcecom
- Salesloft
- Gong
- Chorus
- Sales Processes
- Sales team leadership
- Cross-functional team coordination
Certification
Sandler Essentials Certification
Personal Information
Title: SaaS and Fintech Sales Leader
Timeline
District Sales Manager
Toast
07.2023 - Current
Senior Manager of New Logo Sales
GoCanvas
10.2022 - 07.2023
Senior Manager of Business Development
GoCanvas
05.2022 - 10.2022
Business Development Manager
GoCanvas
05.2021 - 05.2022
Business Development Manager
OnStation - Powered by PROJiTECH
12.2018 - 08.2021
VIP and Partnership Specialist
PlayhouseSquare
08.2010 - 10.2013
Sales Enablement Specialist (North America)
Signet Jewelers
02.2007 - 09.2018
Bachelor's degree -
Kent State University