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
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
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
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
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
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