Nicole Miles
CHICAGO
Summary
Full-cycle B2B SaaS seller with background in customer lifecycle, expansion revenue, and net-new acquisition. Experienced managing multimillion-dollar portfolios and closing revenue across SMB and commercial accounts. Combines deep product knowledge with consultative sales execution to drive measurable growth.
Overview
7
7
years of professional experience
Work History
Account Executive
Smile.io
2025.01 - Current
- Closed ~$648K ARR across 29 net-new accounts (~$22K ACV)
- Maintained 32% win rate; ranked among top SMB net-new contributors
- Owned full sales cycle from qualification to close
- Partnered cross-functionally to support pricing, data, and implementation
Senior Customer Success Manager
Smile.io
2024.01 - 2025.01
- Managed ~$4M ARR portfolio across ~60 accounts; owned expansion revenue
- Closed $600K across 25 upsell/cross-sell deals at a 30% win rate
- Built account growth strategies aligned to customer business goals
- Converted adoption signals into revenue opportunities
- Partnered cross-functionally to accelerate deal cycles and remove blockers
Customer Success Manager
Smile.io
2023.02 - 2024.01
- Drove onboarding, adoption, and lifecycle engagement
- Managed portfolio focused on utilization and customer health
- Supported retention strategy and surfaced expansion opportunities
Implementation Specialist
Smile.io
2022.05 - 2023.02
- Led onboarding and go-live execution for new customers
Support Representative
Smile.io
2022.03 - 2022.05
- Created support resources and introduced new approaches that increased 5-star customer reviews across the team leading to quick promotion
Founder & Owner
Leigh's
2019.06 - 2021.07
- Built and operated a DTC and wholesale food business, leading sales, partnerships, and go-to-market strategy from launch through exit.
- Prospected and secured wholesale partners through direct outreach
- Drove customer acquisition via events, farmers markets, and community partnerships
- Launched ecommerce site with subscription offerings to generate recurring revenue
- Owned pricing and demand strategy across wholesale and DTC channels
- Managed vendor and partner relationships across marketing, operations, and fulfillment
- Structured and executed asset sale of recipes, customer accounts, and equipment after building a profitable DTC and wholesale business
Education
Bachelor of Science - Psychology
California Polytechnic State University
San Luis Obispo, CASkills
Sales & Revenue
Full-cycle sales Expansion & upsell strategy Pipeline generation Consultative selling Negotiation & closing
Customer Lifecycle
Onboarding & implementation Customer adoption Retention strategy
SaaS & Commercial
B2B SaaS sales Subscription revenue models Stakeholder management
Cross-Functional Leadership
Sales–CS alignment Product feedback loops Technical stakeholder coordination Executive communication
Timeline
Account Executive
Smile.io
2025.01 - Current
Senior Customer Success Manager
Smile.io
2024.01 - 2025.01
Customer Success Manager
Smile.io
2023.02 - 2024.01
Implementation Specialist
Smile.io
2022.05 - 2023.02
Support Representative
Smile.io
2022.03 - 2022.05
Founder & Owner
Leigh's
2019.06 - 2021.07
Bachelor of Science - Psychology
California Polytechnic State University