Sr. Director of Inside Sales & Operations

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

Steadily is hiring a Sr. Director of Inside Sales & Operations 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

• Own the Inside Sales & Operations Functions:
  Lead both Inside Sales and Sales Operations as a unified engine aligning people, process, and technology to drive efficient, scalable revenue growth.

• Lead and Scale the Inside Sales Organization:
  Directly manage Sales Managers overseeing licensed inside sales agents; ensure consistent execution, high-quality sales practices, and strong performance across the funnel.

• Architect Sales Operations Strategy:
  Own CRM (Salesforce) architecture, lead routing and scoring, workflow design, and system integrations; build the infrastructure required to scale a high-volume, transactional sales motion.

• Drive End-to-End Funnel Performance:
  Define and manage core KPIs such as speed-to-lead, contact rate, quote-to-bind conversion, premium per policy, retention, and upsell. Implement data-driven strategies to continuously improve them.

• Build World-Class Analytics & Forecasting:
  Develop robust dashboards, cohort analyses, and forecasting models; deliver clear insights to executive leadership on pipeline health, agent productivity, and marketing ROI.

• Develop Leaders and Teams:
  Coach and mentor Sales Managers; implement rigorous hiring, onboarding, training, and QA programs to elevate performance across the organization.

• Optimize Lead Management & Revenue Efficiency:
  Partner with Marketing to refine lead generation, scoring, and distribution; ensure optimal allocation of leads to maximize conversion and ROI.

• Drive Automation and AI Adoption:
  Identify and implement opportunities to automate manual workflows, improve straight-through processing, and leverage AI to increase speed, efficiency, and conversion rates.

• Cross-Functional Leadership:
  Work closely with Product, Engineering, Insurance, and Client Experience to improve product competitiveness, user experience, and operational scalability based on front-line insights and data.

• Own Capacity Planning & Productivity:
  Align hiring plans, staffing models, and agent capacity with demand forecasts; drive improvements in premium per agent and overall unit economics.

Your Background

• Leadership Experience:
  7+ years leading high-volume inside sales organizations, including direct management of Sales Managers and ownership of sales operations.

• Sales & Revenue Operations Expertise:
  Deep experience with CRM systems (Salesforce preferred), lead routing/scoring, workflow automation, and building scalable sales infrastructure.

• Performance-Oriented Operator:
  Proven track record of improving conversion rates, increasing productivity, and exceeding revenue targets in fast-paced, transactional environments.

• Analytical & Data-Driven:
  Strong ability to build dashboards, interpret funnel metrics, and translate data into actionable strategies.

• Operational Excellence:
  Experience designing and optimizing processes across the full sales lifecycle, including capacity planning and forecasting.

• Technology & Automation Mindset:
  Familiarity with sales engagement tools, dialers, analytics platforms, and emerging AI-driven sales workflows.

• Insurance or Complex Product Experience (Preferred):
  Background in Property & Casualty insurance or similarly regulated, complex products is a strong plus.

• People Developer:
  Demonstrated ability to build, scale, and develop high-performing teams and leaders in a 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!