Job Location: Chicago, IL, hybrid in-office schedule

Requirements: 10 years of experience, 5 years of sales management experience

Organization Summary

Based in downtown Chicago, Trajektory is an innovative data insights and valuation technology startup. The company has a unique approach to leveraging and valuing sponsorship data in the sports, media, and entertainment industries. The founders are former executives from various sports, media, and entertainment organizations, including the NFL, NBA, MLB, NHL, NCAA, WNBA, AFL, and e-sports.

Trajektory prioritizes company culture and supports both the personal and professional development of its employees. The company was built by former leaders who enjoy working hard and having fun. A deep appreciation for data analytics and a passion for building close-knit teams are core values. The company promotes a culture of belonging, curiosity, and development. The leadership team is interested in allowing individuals to grow in their careers and hopes employees will stay for the rest of their careers. A "nerdy sense of humor" is a plus, and a fascination with data is a must

The Role

This is a player/coach sales leader position where you will manage and oversee the day-to-day operations of the sales team. Your main objective will be to streamline operational efficiency through process, planning, and tactical execution. You are expected to both manage the team and contribute to building and executing the company's sales goals. The ideal candidate has a history of managing teams, is "sales-obsessed" and has a deep understanding of sponsorship and data storytelling. You must also be able to manage and navigate multiple complex projects across several internal departments simultaneously.

This role is a key member of the leadership team, and you will be expected to help build the company culture rather than just fitting into an existing one. We are looking for someone who has successfully grown a sales operation from a revenue of $3M-$5M to at least $15M. This performance is preferably from an early-stage company. However, a candidate who has grown a district or regional sales operation by this amount at a larger software company may also be a good fit. You should also have a proven track record of hiring new quota-carrying representatives who then meet their sales targets. You must be aggressive and obsessive about determining the competitive landscape for each deal, and set strategies accordingly, with a particular focus on competitor sales tactics.

Responsibilities:

• Coach, support, and develop the sales team, which currently consists of four people including sales managers and BDRs.
• Set best practices for sales messaging, discovery, objection handling, and closing techniques.
• Foster a high-performance, feedback-driven culture with clear accountability.

Quota-Carrying Sales Execution

• Directly manage a subset of high-value opportunities or strategic accounts.
• Act as a lead closer on top-tier deals, particularly for enterprise or complex negotiations.
• Serve as an escalation point for sales conversations that require senior credibility.

Tactical Revenue Leadership

• Design and implement the overall revenue strategy and related tactics for all new business.
• Define target market segments and ideal customer profiles (ICPs), and implement the go-to-market approach for each core industry.
• Align revenue goals with company objectives, such as ARR growth and brand focus.

Analytical & Technical Mastery

• Own all sales data reporting and insights, and work with other teams such as marketing and business intelligence.
• Have deep technical knowledge of sales enablement tools like Excel and Salesforce.
• Manage sales reports and forecast projections for company leadership and board meetings.
• Actively lead and monitor demand generation activities.

Sales Process Ownership

• Define categories, territories, quotas, compensation plans, and org structure as the team grows.
• Own and refine the end-to-end sales process, from lead qualification to closed-won deals.
• Ensure CRM hygiene and accurate forecasting.
• Identify and eliminate bottlenecks in the sales funnel.

Cross-Functional Collaboration

• Partner with the Marketing department to develop and align campaigns with revenue goals.
• Collaborate with the Product team to relay customer feedback and inform the product roadmap.
• Align with Customer Success for upsell/cross-sell opportunities and churn reduction, including providing feedback on pricing strategies.
• Provide executive-level visibility on pipeline health, win/loss insights, and strategic risks.

Qualifications:

• 10+ years of strong experience in a B2B SaaS analytics role, preferably at an early-stage startup or growth company.
• 5+ years of experience managing a team of at least three people.
• While overall software experience is acceptable, experience selling an analytical solution (or a component of the marketing tech stack) to the Chief Marketing Officer (CMO) is highly preferred.
• Experience with project management software (e.g., Asana, Airtable) and CRM systems (e.g., Salesforce, Hubspot).
• Must be extremely organized, proactive, and data-driven.
• The ideal candidate is a self-starter who acts as the "CEO of their business division".
• Proven success managing teams, balancing stakeholder needs, and working under tight timelines with resource constraints.
• Must be able to forge genuine and lasting internal and external relationships.
• Demonstrated success in managing multiple customer and senior executive relationships.
• Demonstrated success managing sales department core competencies including leadership, customer relations, and data analysis.
• Relevant B2B SaaS sales experience with the ability to participate in conversations with various levels of customer contacts.
• An expert in organization, process building, and knowledge of CRM software.
• Monthly travel is required.
• Leads with integrity.
• Must be a "good human".

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Accounting/Auditing and Finance

• Industries

  Technology, Information and Media

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