Regional Sales Manager

Posted Yesterday
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Hiring Remotely in Chicago, IL, USA
Remote or Hybrid
165K-185K Annually
Senior level
Information Technology • Insurance • Professional Services • Software • Analytics
We are an integrated insurance, risk, safety, and compliance solution for responding to real-world challenges.
The Role
Manages and coaches a team of enterprise SaaS sales representatives, ensuring quota attainment, prospecting, pipeline development, CRM adoption, and consistent sales-process execution. Develops territory and pipeline strategies, provides market and competitive guidance, collaborates with Sales Operations and Marketing, supports hiring, and drives strategic sales initiatives. The role requires strong consultative selling expertise, data-driven coaching, and up to 25% travel.
Summary Generated by Built In
Overview

The Regional Sales Manager is a front line manager who reports to our VP of Sales. You are someone who understands the science of selling and have successfully managed enterprise SaaS Sales representatives. You will be responsible for managing a team of high-performing sales professionals who are engaged in selling the Integrated Risk Management software products and services offered by Origami Risk and its subsidiaries. You will be responsible for ensuring that your team is always focused on the right activities to ensure a sustainable sales pipeline to achieve company sales goals. You are responsible for providing technical and metric driven support for your team to ensure continuity in the execution of a single sales process.


Starting base pay for this role is between $165,000 and $185,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states).

Responsibilities
  • Continues the tradition of building a positive, success-driven corporate culture that has led Origami Risk to be the leader in multiple SaaS markets.
  • Accountable for the sales success of a team of experienced, high-performing Sales Executives, by ensuring Sales representatives achieve annual sales targets.
  • Manages consistent prospecting and pipeline development of each team member through individual territory plans.
  • Provides coaching and oversight of all sales executives to ensure productivity and quality using Origami’s sales process.
  • Ensures the use of the Company’s policies and procedures, including use of CRM, documentation, interaction with other departments such as Product, Legal, Recruiting, HR, Finance and Professional Services.
  • Collaborates with Sales Operations and Marketing to ensure that Origami’s entire marketing, lead generation and sales process are consistently aligned.
  • Assesses the strengths and weaknesses of your team and manages the sales program accordingly through guidance, coaching, mentoring and staffing.
  • Implements a strategy for developing and maintaining a strong, consistent pipeline of prospective customers.
  • Acts as a subject matter expert for your team on what they face in the market from competitors on their opportunities, and executes tactics to successfully win.
  • Assists in the continual management of hiring pipeline of Sales representatives, including conducting interviews, assessments and providing feedback on candidates.
  • Accountable for strategic and tactical initiatives throughout the year as directed by the Director of Sales.
Qualifications
  • Bachelor’s Degree Required.
  • 3+ Years of Sales Management Experience.
  • 5+ Years of Direct Sales Experience.
  • Familiarity with a highly consultative Sales process, such as MEDDPICC.
  • Excellent coaching skills: ability to observe, evaluate and give meaningful feedback.
  • Strong data analytical skills using Salesforce, DemandBase and other supporting systems.
  • Strong verbal and written communication skills.
  • Familiarity with Salesforce CRM.
  • Remote work permitted, but preferred proximity to Chicago.
  • Up to 25% travel required.
Benefits
  • Medical and Dental coverage available for employees, dependents, domestic partners, and spouses
  • Paid Time Off – Flexible options plus 10 paid company holidays where available**
  • All full-time positions are hybrid, with many eligible to be completely remote
  • Fully Paid by Origami Risk – Vision insurance, Short & Long-Term Disability Insurance, and Basic Life Insurance
  • Generous family leave options—including adoption and foster care placements
  • Pre-Tax Savings Accounts – Flexible Spending Account, Health Savings Account, Commuter Benefits, Dependent Care Savings Account
  • Retirement Savings – 401(k) with company match up to 4%
  • Employee Assistance Program (EAP) – Confidential & Free support offered to colleagues facing personal or work-related complications
  • Education Assistance Program – to help colleagues pursue industry/role-specific certifications
  • Wellness Benefits – reimbursement program to invest in healthy habits as well as support better colleague productivity and stress management
  • Additional coverages available – Pet Insurance, Critical Illness Insurance, and Voluntary Life & AD&D coverage
**Flexible PTO not available in California or the UKWho We Are

Origami Risk delivers single-platform SaaS solutions that help organizations best navigate the complexities of risk, insurance, compliance, and safety management.


Founded by industry veterans who recognized the need for risk management technology that was more configurable, intuitive, and scalable, Origami continues to add to its innovative product offerings for managing both insurable and uninsurable risk; facilitating compliance; improving safety; and helping insurers, MGAs, TPAs, and brokers provide enhanced services that drive results.


A singular focus on client success underlies Origami’s approach to developing, implementing, and supporting our award-winning software solutions. 


Origami Risk is proud to be an equal opportunity employer. We thrive and benefit from diversity and are committed to creating an inclusive and equitable environment for all employees. We do not discriminate against any individual based upon race, religion, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, color, sex, national origin, age, marital status, military or veteran status, disability, or any other characteristic protected by applicable law.


Caution: Be alert to recruiting scams. We have received reports of individuals impersonating Origami Risk recruiters to deceive candidates into disclosing personal information. These impostors use fake Origami Risk domain names and email addresses. Please double-check that any email address from an Origami Risk recruiter ends with origamirisk.com or talent.icims.com. And to confirm the legitimacy of any recruiting communication, feel free to email [email protected].

Skills Required

  • Bachelor's degree
  • 3+ years of sales management experience
  • 5+ years of direct sales experience
  • Familiarity with a highly consultative sales process, such as MEDDPICC
  • Excellent coaching skills, including observing, evaluating, and providing meaningful feedback
  • Strong data analytical skills using Salesforce, DemandBase, and supporting systems
  • Strong verbal and written communication skills
  • Familiarity with Salesforce CRM

Origami Risk Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Origami Risk and has not been reviewed or approved by Origami Risk.

  • Healthcare Strength Medical and dental options are complemented by 100% company‑paid vision, disability, and life insurance, plus mental health benefits. Wellness reimbursement and a fitness stipend further reinforce health support.
  • Leave & Time Off Breadth Flexible/unlimited PTO is paired with paid holidays, sick time, volunteer time, and bereavement leave. This breadth provides extensive coverage for rest and personal needs.
  • Parental & Family Support Up to 12 weeks of paid parental leave is available alongside childcare benefits and family medical leave. A mother’s room and flexible work arrangements support family needs.

Origami Risk Insights

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The Company
HQ: Chicago, IL
900 Employees
Year Founded: 2009

What We Do

Origami Risk empowers leaders in insurance, risk, and safety with a purpose-built, cloud-native platform that optimizes workflows for better data, better insights, and better collaboration. Through highly configurable solutions integrated on a single platform, Origami Risk supports the management of the full lifecycle of risk, from prevention to recovery—helping the experts reduce harm and loss, and respond more rapidly and effectively when it happens. Grounded in continuous innovation and a foundational focus on client success, Origami Risk is trusted by leading organizations to enable greater resilience as they build for the future. For more information, visit origamirisk.com

Why Work With Us

It all begins with our people. Our success is made possible by our team—individuals who are looking to take ownership of issues, display keen problem-solving ability, have the ability to work collaboratively, and possess an eagerness to learn and to share knowledge. We've built and maintained a strong culture with those who share these ambitions.

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