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Rachel Brenner

@rachelbrenner

Channel sales leader at When Insurance who built broker partnerships and repeatable referral pipelines.

At When Insurance, I built and scaled channel partnerships, developed the broker ecosystem, and created repeatable referral pipelines. I also activated strategic and marketplace partnerships to support go-to-market and additional attachment strategies.

At Paychex, Inc., I managed a portfolio of more than 20 products and executed product strategy from concept through launch. Product enhancements improved customer satisfaction by 15%, and product revenue increased by 20%.

Earlier, I developed sales enablement programs at Paychex, Inc. and Oasis Outsourcing, including playbooks, training, and CRM implementation support. At Oasis Outsourcing, I also developed an insurance broker referral network that consistently fulfilled 35% of annual quota.

Experience

Work history, roles, and key accomplishments

Channel Sales Manager

When Insurance

Jul 2025 - Aug 2026 (1 year 1 month)

Drove channel-based revenue growth by building and scaling partnerships, creating repeatable referral pipelines, and activating strategic partnerships to improve lead conversion.

Channel Sales Partnership Development Broker Ecosystem GTM Strategy Lead Conversion

Product Strategy Manager II

Paychex, Inc.

Oct 2019 - Feb 2025 (5 years 4 months)

Managed a portfolio of over 20 products, driving strategic initiatives and product enhancements that improved customer satisfaction by 15% and increased product revenue by 20%. Led GTM strategies for six acquisition integrations and collaborated with development teams on technical integration and project scoping.

Product Strategy Product Management GTM Strategy Vendor Management Market Analysis Cross Functional Collaboration Confluence Net Promoter Score

Sales Enablement Analyst II

Paychex, Inc.

Apr 2019 - Sep 2019 (5 months)

Developed targeted sales campaigns and enablement materials, trained new reps, and implemented CRM features that boosted sales rep productivity by 30% and improved conversion rates by 15%.

Sales Enablement Sales Training CRM Salesforce Confluence sales playbooks Pricing Models

Enablement and Training Consultant

Oasis Outsourcing

May 2016 - Apr 2019 (2 years 11 months)

Developed and implemented training materials, coached new reps to reduce time to sale by 15%, and trained a national sales force of 100 on a new CRM and proposal system.

Training Sales Enablement Coaching CRM Implementation Onboarding Presentation Skills

Senior Business Consultant

Progressive Employer Management Company

Apr 2014 - Mar 2016 (1 year 11 months)

Exceeded annual business development sales targets by 20% and nurtured a broker ecosystem that referred consistent business.

Business Development Sales Broker Development Relationship Management

Regional Sales Consultant

TriNet

May 2013 - Apr 2014 (11 months)

Achieved bonus level by surpassing annual sales target by 10% in the first year.

Sales Business Development B2B Sales

PEO Sales Manager

Trigen Group

Oct 2012 - Jan 2013 (3 months)

Increased partnerships by 100% by cultivating strategic relationships with 5 new active brokers in 2 months, and managed new PEO business resulting in a 15% revenue increase.

Sales Management PEO Broker Development Strategic Partnerships Revenue Growth

President and Owner

Prodigy, Inc.

May 2011 - Oct 2012 (1 year 5 months)

Founded and operated a startup brokerage for PEO and payroll services.

entrepreneurship Business Management PEO Payroll Services

Sr. Consultant/District Sales Supervisor

Oasis Outsourcing

May 1999 - May 2011 (12 years)

Sold the largest client (2000 WSE) within two years, bringing in $1.5 million in revenue, and built a client portfolio generating over $2 million in revenue. Led a sales team with consistent performance and weekly reporting.

Sales Business Development Client Portfolio Management Team Leadership Referral Networks Revenue Growth