Destination Manager Jobs in Chicago, IL (NOW HIRING)

Who You Are

The Sales Manager is the engine of this sales team. You are not a scorecard reviewer or a meeting facilitator. You are a coach, an accountability partner and a culture driver. You are in it every single day: on calls, in 1:1s, side by side with your reps and always looking for the next opportunity to make someone better. You lead from the front and you never ask your team to do something you wouldn't do yourself.

• The Coach: You live for the development conversation. You observe, you listen, you give feedback that sticks and you follow up. You know that real coaching happens in the moment, not just in a scheduled session.
• The Accountability Partner: You hold the standard without apology. You track performance, have the hard conversations early and follow the accountability process with consistency and fairness. Your team always knows where they stand.
• The Culture Driver: You set the tone every single day. High energy, high expectations and an unwavering belief in your team's ability to win. You celebrate the wins, own the losses and never let the team go cold.
• The Operator: You run tight cadences, show up prepared and make every touchpoint with your team count. You don't wing it. You plan your week, execute your process and create the kind of rhythm that high-performing teams thrive in.

Key Responsibilities

1. Coaching & Individual Development

• Conduct weekly face-to-face 1:1s with every consultant. Covering scorecard performance, call feedback and a targeted skill-building activity
• Complete a minimum of 2–3 call observations per rep per week with a completed observation form for every call
• Conduct live side-by-side sessions for any rep performing below 80% overall scorecard, minimum once per week
• Document every coaching session within 24 hours, including summary, skill activity, implementation status, next steps and commitments made
• Follow up on skill implementation every rep leaves every 1:1 knowing exactly what they are working on and every manager knows whether it landed

2. Performance Accountability

• Own the full accountability process from documented verbal discussions to PIPs, 30-day reviews and exit criteria
• Review scorecards and ensure every rep is fully aware of where they stand, nothing comes as a surprise
• Identify performance trends early and intervene before a gap becomes a pattern
• Maintain all coaching and accountability documentation in the designated system current, complete and accessible
• Exit the accountability process on clear terms a rep must sustain 80%+ for a full quarter before formal status is lifted

3. Team Cadences & Pipeline Management

• Facilitate bi-weekly L10 team meetings with a prepared agenda, covering performance, wins, issues and team alignment
• Run multiple 15-minute pipeline stand-ups throughout the week every rep leaves knowing their pipeline status and their next actions
• Use stand-ups to identify who needs support, who is tracking well and where urgency needs to be created, in real time
• Maintain full visibility into every rep's pipeline at all times, not just at check-in

4. Culture & Team Engagement

• Set the tone every day energy, expectations and belief in the team are non-negotiable
• Celebrate wins publicly and consistently on the scoreboard and in the room
• Create an environment where reps feel seen, supported and challenged to grow
• Partner with the Enablement Specialist to bring learning into the culture, not just into formal training sessions
• Champion the team's success in every cross-functional conversation, advocate for your people

5. Cross-Functional Collaboration

• Partner with the Sales Enablement Specialist to identify skill gaps and ensure training is deployed and adopted
• Coordinate with the Sales Ops Manager on tool usage, process adherence and Sales Assistant’s workflow standards
• Provide the Director of Sales with regular, transparent updates on team performance, coaching activity and key risks
• Participate in cross-functional discussions that impact the sales team and bring the team's voice to the table

• 3+ years of experience in a sales role with at least 1-2 years in a team lead, senior or management capacity
• Proven track record of coaching sales reps to measurable performance improvement
• Deep understanding of consultative selling and the ability to model and teach it in real time
• Strong command of pipeline management, forecasting and performance metrics
• Experience executing structured accountability processes PIPs, performance conversations and documentation
• Ability to run high-energy, efficient team cadences that drive action not just conversation
• High emotional intelligence, you can read a room, have hard conversations with care and build trust quickly
• Comfort with CRM tools, scorecards, and sales reporting
• Experience working within the Entrepreneurial Operating System (EOS) is a strong plus