Director of Inside Sales

Location: Overland Park, KS (Kansas City Metro)Employment Type: Full-time, In-OfficeDepartment: SalesSalary: Top of market base salary + equity

Steadily is hiring a Director of Inside Sales in the Kansas City Metro area who is the very best at what they do. The Director of Sales will lead the strategy and execution of sales operations for the inside sales team.

This is a full-time, in-office position based in Overland Park, KS.

What You’ll Do

• Lead the Inside Sales Team: Directly manage a team of Sales Managers who oversee Steadily’s licensed inside sales agents, ensuring high performance, sales quality and consistent execution across the entire funnel.

• Drive Sales Operations Forward: Lead the strategy and execution of sales operations for the inside sales team — lead routing and scoring, performance dashboards, reporting, and process optimization.

• Own the End-to-End Sales Performance: Set and monitor KPIs for the entire sales organization — speed-to-lead, quote-to-bind conversion, premium per policy, upsell effectiveness — and implement strategies to improve them.

• Develop Leaders: Coach and mentor Sales Managers on people leadership, performance management, and process improvement; implement consistent training and QA standards across teams.

• Forecast and Report: Build and maintain detailed dashboards and pipeline forecasts; deliver actionable insights and recommendations to senior leadership on conversion trends, agent productivity, and campaign ROI.

• Cross-Functional Collaboration: Work closely with Marketing, Insurance and tech Product teams, and Client Experience to improve messaging, product competitiveness, and coverage options based on front-line feedback and data.

• Scale and Automate: Identify opportunities to automate manual workflows, enhance systems integrations, and improve the experience for both agents and prospects.

Your Background

• Leadership Experience: 5+ years leading high-volume inside sales organizations with direct management of Sales Managers and responsibility for sales operations.

• Sales Operations Expertise: Deep knowledge of CRM configuration (Salesforce preferred), lead scoring/routing, reporting, and process design in a high-volume environment.

• Performance Driven: Track record of exceeding quotas and improving conversion metrics across large, transactional sales teams.

• Operational Acumen: Comfortable designing workflows, setting KPIs, and leveraging sales engagement tools (dialers, email automation, analytics) to drive results.

• Insurance Knowledge: Experience in Property & Casualty insurance or other regulated, complex products is a strong plus.

• People Developer: Skilled at motivating and developing both front-line managers and their teams in a fast-growth environment.

Compensation and Benefits

• Compensation: Top of market salary

• Equity: Stock options in a fast-growing company

• Time Off: 3 weeks PTO + 6 federal holidays

• Insurance: Medical, dental, vision, life, disability, HSA, FSA

• Retirement: 401(k)

• Perks: Free snacks, team lunches, collaborative office culture

Location

• Overland Park, KS

• Steadily is building a workplace environment of team members who are passionate and excited to be together in person. Our office is in Overland Park, and is key to our fast-paced growth trajectory.

Why Join Steadily

• Good company. Our founders have three successful startups under their belt and have recruited a stellar team to match.

• Top compensation. We pay at the top of the Kansas City market (see comp).

• Growth opportunity: We’re an early-stage, fast-growing company where you’ll wear a lot of hats and shape product decisions.

• Strong backing. We’re growing fast, we manage over $20 billion in risk, and we’re exceptionally well-funded.

• Culture: Steadily boasts a very unique culture that our teammates love. We call it like we see it and we’re nothing if not candid. Plus, we love to have a good time. Check out our culture deck to learn what we’re all about.

• Awards: We've been recognized both locally and nationally as a top place to work. Recently we were ranked 16th on Forbes' 2026 Best Startup Employers list, and 63rd on the prestigious Inc 5000 Fastest Growing Companies list. We've also been recognized as one of the Best Landlord Insurance Companies in 2026 by CNBC, a Top 2025 Startup in Newsweek, in Investopedia's Best Landlord Insurance Companies, and we won Austin Business Journal's Best Places to Work in 2025.

We’re excited to meet you!