Senior Manager of Inside Sales

World's Finest Chocolate•Chicago, IL

12d•$131,000 - $145,000•Remote

About The Position

World’s Finest Chocolate does more than make delicious chocolate. Since 1949, we’ve helped our fundraising customers raise over $4.7 billion! These funds are used to buy playgrounds, pay for reading specialists, purchase musical instruments, fund field trips, and more. Our employees work as a team to support our company’s mission: To Deliver Extraordinary Value with Fun & Purpose. We are seeking a Senior Manager of Inside Sales – Fundraising to lead, energize, and transform our remote inside sales channel. This leader will oversee Inside Sales Managers , who in turn will manage and develop Inside Sales Representatives. The Senior Manager will be accountable for revitalizing a team that has plateaued, by introducing new systems, playbooks, and leadership practices that drive measurable performance improvements. The ideal candidate will be a highly organized, metrics-driven driver with a proven track record of leading remote/inside sales organizations to sustained success. This person will innovate virtual fundraising strategies, strengthen market penetration in underdeveloped territories, and build scalable systems that accelerate revenue growth. This role carries a $15MM revenue goal in year one , with a plan for aggressive expansion in subsequent years.

Requirements

10+ years of sales leadership, with at least 5 years in a Senior Manager-level role leading inside sales teams.
Proven success leading remote/inside sales organizations to high performance and revenue growth.
Strong expertise in virtual selling models, sales technology, and pipeline management.
Experience in assessing teams, making quick decisions, and implementing structural improvements.
Excellent communication, coaching, and organizational skills with a hands-on leadership style.
Bachelor’s degree required

Nice To Haves

MBA preferred.

Responsibilities

Design and execute inside sales strategies that align with company growth goals.
Build and refine a remote sales playbook designed for virtual fundraising success.
Identify opportunities to penetrate underserved markets and expand brand awareness through innovative outreach.
Establish, monitor, and continuously improve key inside sales performance metrics (conversion rates, call volumes, close rates, retention).
Leverage systems and infrastructure to streamline workflows, optimize pipelines, and track results.
Implement sales contests, promotions, and recognition programs tailored to remote selling environments.
Contribute to sales forecasting accuracy by delivering timely and reliable performance data, pipeline updates, and insights that support senior leadership in revenue planning.
May provide regular performance reporting to senior leadership, summarizing sales trends, KPI results, and actionable insights drawn from dashboards and pipeline data.
Hire, train, and coach Inside Sales Managers to ensure their teams achieve and exceed targets.
Partner with Training & Development to create impactful onboarding and ongoing learning programs tailored to remote sales.
Assess team performance quickly, making decisive changes to improve capability, engagement, and productivity.
Recommend and implement systems, tools, and technology that improve inside sales effectiveness.
Introduce scalable processes and reporting infrastructure to ensure transparency and accountability.
Collaborate cross-functionally with Marketing, Operations, and Finance to ensure alignment on lead generation, campaigns, and goals.
Ensure effective use of Salesforce across the Inside Sales organization by establishing clear data-entry standards, training managers and representatives, and monitoring compliance to maintain accurate, actionable sales pipeline reporting.