Summary
Overview
Work History
Education
Skills
Certification
Timeline
Generic

Kyle Maines

Falmouth,ME

Summary

Dynamic Senior Manager with a proven track record at Guideline, specializing in onboarding strategy and KPI development. Achieved a 61% reduction in customer onboarding time through innovative process automation and team mentoring. Adept at fostering cross-functional collaboration to enhance client experiences and drive revenue growth. Passionate about empowering teams to excel.

Overview

2026
2026
years of professional experience
1
1
Certification

Work History

Senior Manager, Customer Onboarding

Guideline
Burlingame, CA
09.2024 - Current
  • Designed and implemented a new onboarding operating model focused on plan activation and revenue alignment, improving forecasting accuracy and strategic resource planning.
  • Led strategic shift from support-based metrics to activation-focused KPIs, contributing to a 61% reduction in TTR and 16% drop in stall rate for high-value clients.
  • Created and executed initiatives to support an 80% forecasted increase in plan volume, including process improvements, interdepartmental coordination, and automation pilots.
  • Developed and scaled a cancellation saves playbook, preserving over $44K in ARR in a single quarter.
  • Mentored and empowered team managers through structured delegation, growth plans, and leadership-focused development check-ins.
  • Established recurring leadership forums and cross-functional partnerships with Product, Sales, and Legal to drive execution and alignment across onboarding priorities.

Onboarding Specialist

Guideline
Burlingame, CA
07.2018 - 08.2019
  • Managed end-to-end onboarding for new and converting 401(k) plans, ensuring a seamless transition from Sales to Customer Success.
  • Developed and refined workflows for client handoffs and internal processes, improving consistency and operational efficiency across the onboarding team.
  • Built and maintained strong relationships with financial advisors, delivering a high-touch onboarding experience, and strengthening Guideline for Advisors’ reputation for service excellence.
  • Maintained high attention to detail, minimizing onboarding errors, and reducing downstream escalations, directly supporting team OKRs for issue reduction.
  • Collaborated cross-functionally to identify and resolve onboarding challenges early, improving time to activation and long-term plan health.

Manager, Customer Onboarding

Guideline
Burlingame, CA
  • Led hiring, onboarding, and training of new team members to support team growth and maintain service levels.
  • Revamped training and documentation, cutting ramp time by 40% and boosting new hire autonomy.
  • Launched department-wide initiative focused on activation that reduced attrition and generated $500K+ in additional revenue.
  • Built strong cross-functional partnerships to streamline workflows and resolve integration issues.
  • Created onboarding SOPs and templates, saving 320+ hours/year and improving consistency.
  • Redesigned phone support process, cutting wait time by 30% and abandonment by 25%.
  • Developed cost-to-serve model and time audit to guide resourcing and strategic planning.
  • Led onboarding through peak seasons, achieving KPI targets and improving client outcomes.

VP, Client Manager & Recruiter

Smith & Wilkinson
Scarborough, ME
10.2016 - 04.2018

Project Coordinator

Smith & Wilkinson
Scarborough, ME
02.2016 - 10.2016

Golf Professional & Coach

Poland Spring Resort
Poland, ME
05.2012 - 01.2016

Education

Bachelor of Science - Business Administration And Management

Coastal Carolina University
Conway, SC
12-2014

Skills

  • Onboarding strategy
  • KPI development
  • Process automation
  • Data analysis
  • Team mentoring
  • Customer relationship management
  • Cross-functional collaboration

Certification

  • Chartered Retirement Plans Specialist (CRPS)

Timeline

Senior Manager, Customer Onboarding

Guideline
09.2024 - Current

Onboarding Specialist

Guideline
07.2018 - 08.2019

VP, Client Manager & Recruiter

Smith & Wilkinson
10.2016 - 04.2018

Project Coordinator

Smith & Wilkinson
02.2016 - 10.2016

Golf Professional & Coach

Poland Spring Resort
05.2012 - 01.2016

Manager, Customer Onboarding

Guideline

Bachelor of Science - Business Administration And Management

Coastal Carolina University

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