Mid-Market Sales Representative

Benchmark Analytics; Chicago (IL); On-site; USD 70,000 - 75,000; Full time

Benefits offered by this job

Unlimited PTO

Fully remote in US

Summer Half-Day Fridays

Medical, dental, and vision

401(k)

Life insurance

Job summary

Benchmark Analytics is expanding its Mid-Market team and seeking a proven SaaS salesperson who thrives on outbound prospecting and closing deals.

You will own the full sales cycle—from discovery to demonstration, proposals, negotiation, and close—building a scalable playbook with the VP of Mid-Market Sales. This is a remote role with travel up to 25%; Chicago-based candidates are preferred. Competitive salary, benefits, and unlimited PTO.

Qualifications

• 2+ years SaaS sales experience.
• Proven track record of meeting or exceeding sales goals.
• Experience selling into government or regulated industries preferred.
• This is a remote role with up to 25% travel; Chicago-based preferred.

Responsibilities

• Build and manage a healthy pipeline of Mid-Market opportunities through outbound prospecting.
• Own the full sales cycle from discovery through close, including demos and proposals.
• Develop champions within prospective accounts and build stakeholder relationships.
• Maintain accurate pipeline and forecasting in Salesforce and meet sales targets.
• Help shape the mid-market playbook, messaging, and process as we scale.

Skills

SaaS sales

Outbound prospecting

Pipeline management

Negotiation

Communication

Tools

Salesforce

CRM

Job description

Who We Are:

Dedicated to making a difference in law enforcement agencies across the U.S., our mission is to transform policing by elevating officer performance with a preventative-based early intervention system. Driven by data science and powered by machine learning, our offering analyzes officer performance data in order to identify potentially problematic behavior. In partnership with the University of Chicago, we’ve developed the world’s largest multi-jurisdictional officer performance database, and the only research-driven, evidence-based early intervention system available in policing today. We’re also the only provider of a fully integrated, cloud-based Software-as-a-Service (SaaS) platform that simplifies essential policing workflows. This platform is designed to be a single-source solution for all operational needs, driving extensive efficiency gains and providing best-in-class advanced analytics and insights. Benchmark Analytics provides a comprehensive, all-in-one solution that is advancing police force management through state-of-the-art technology and market-leading data and analytics.

The Role:

Benchmark Analytics already partners with some of the largest police departments in the country, and we're now launching a Mid-Market segment to bring that same impact to police departments of every size, and we're hiring the first few people to build it. This is a true ground-floor opportunity, and a full-cycle role with a strong emphasis on outbound prospecting and new customer acquisition. There is no established mid-market playbook yet; you will help build it alongside the VP, Mid-Market Sales. We're looking for a proven SaaS salesperson who knows how to hunt for new business, self-generate pipeline through consistent outreach, and is drawn to the chance to shape a new motion rather than execute one that already exists, backed by a company with real, proven traction at the enterprise level. This person should be comfortable demonstrating software and excelling in an environment where activity, accountability, and results matter.

Responsibilities:

• Build and manage a healthy pipeline of Mid-Market opportunities through consistent outbound prospecting.


• Own the full sales cycle from initial prospecting and discovery through software demonstrations, proposal, negotiation, and close.


• Build relationships with multiple stakeholders throughout the sales process and develop champions within prospective accounts.


• Maintain consistent sales activity while effectively managing multiple opportunities at different stages of the sales cycle.


• Maintain accurate pipeline, activity, opportunity, and forecasting information within Salesforce.


• Meet or exceed established sales goals and performance metrics.


• Work closely with the team to actively shape the mid-market sales playbook, messaging, and process as we learn what works.

Job Qualifications:

• 2+ years of successful SaaS sales experience.


• Demonstrated track record of sales achievement, including consistently meeting or exceeding sales goals and/or recognition as a top producer.


• Direct experience selling in an early-stage, or newly-launched motion – not just working within one that was already built.


• Comfortable operating without a mature playbook, established case studies, or reference customers, and motivated to create those assets rather than rely on them.


• Ability to thrive in a growing organization where sales processes and best practices continue to evolve.


• Self-motivated, competitive, coachable, and comfortable being held accountable to activity and performance metrics.


• Proven experience generating new business through outbound prospecting, self-generated pipeline, and full sales cycle management.


• Experience selling into government, GovTech, public safety, law enforcement, or other highly regulated industries is preferred, but not required.


• This is a remote role and requires up to 25% travel; Chicago-based preferred.

What we offer:

• A competitive salary and benefits package.


• Unlimited Paid Time Off.


• Ability to work in a fully remote environment (must be based in the U.S. and willing to work in Central Time Zone).


• Summer Half-Day Fridays.


• Freed Up Fridays during Spring, Fall, and Winter months to promote productivity and dedicated heads-down work time.


• Medical, dental, and vision plan offerings along with 401(k).


• Employer-paid Short-Term Disability, Long-Term Disability, and Life Insurance.


• Other Voluntary Benefits include additional Life Insurance, Spouse Life Insurance, and Accident Insurance.


• The satisfaction that comes with being part of a solution that has real impact in the world.


• A diverse workforce and inclusive environment that embraces unique contributions and experiences.


• An empowered culture that encourages creativity and professional growth.

Estimated Annual Salary Range:

• $70,000-75,000 base salary / $140,000-150,000 OTE; based on role, experience, and location

Additional Information:

• Benchmark Analytics is an Equal Opportunity Employer. We value diversity of all kinds in our effort to create a stellar workforce of committed and passionate team members.


• Unfortunately, we are not able to sponsor employment visas at this time, so we can only accept applications from candidates who are authorized to work in the U.S