Senior Sales Representative (Potential Head of Sales)

Imagine if you had to do your job with no data, no tool, no visibility into performance, and no support. This is what marketing and sales teams experience daily when it comes to quantifying the execution of their go-to-market story and messaging. They have to operate in the blind. Nowhere else in the modern organization is this the case, yet it sits at the center of any company’s go-to-market motion. And in most cases, it’s the difference between winning and losing. It’s time to change this, so let’s fix it together.

Our Vision: To empower every organization and its people with the ability to confidently say the right thing. Today, it means we’ve built the first-ever messaging attribution and persuasive language analysis engine. Tomorrow, it means we’re building the first-ever AI go-to-market story intelligence layer.

We are hiring a senior sales representative with a potential path to future head of sales. You will work directly with the CEO & Co-founder, as well as Troupe’s star-powered Advisors. You’ll report to the CEO.

This is a highly impactful role where your daily work materially impacts our direction.

• Own the full sales cycle — prospecting, outreach, discovery, demo, proposal, negotiation, and close. This role combines the responsibilities of a BDR, SDR, and Account Executive into one seat. You hunt. You qualify. You close.
  
• Build your pipeline from scratch. You’ll have inbound Leads generated from our Marketing efforts and Sales events, but you won’t rely on them to bring you your business. You’ll help identify target accounts, develop your outreach strategy, and go get them, in addition to taking the reins on inbound Leads. This is a hunting role at its core.
  
• Partner with the CEO to close accounts whether generated by you or the CEO. Partner with the CEO to lead outreach and discovery with prospects identified by the CEO. Lead and support in-person sales events alongside the CEO, then run with Leads from those events.
  
• Sell into mid-market accounts, with a primary focus on Marketing and Sales teams who are ready to take control of their go-to-market story and messaging intelligence.
  
• Track and report on pipeline health, deal stages, and forecast with precision. You own your number and know where every deal stands at all times.
  
• Represent Troupe in the market with confidence, clarity, and conviction. You understand the product deeply enough to lead complex, consultative sales conversations and earn credibility with senior buyers.
• Partner with the CEO to build and refine Troupe’s sales process from the ground up. This isn’t a role where you inherit a rigid playbook — it’s an opportunity to help write it.
• Contribute to the evolution of Troupe’s go-to-market playbook. Your field experience will directly shape our messaging, ICP definition, objection handling, & competitive positioning.
• As Troupe scales, help shape what a high-performing sales org looks like — with the potential to lead and coach future team members as the function grows, if desired.

• 5+ years of full-cycle sales experience — you’ve done your own prospecting, pipeline development, and closing. You’ve handled the full funnel, not just one piece of it.
• Proven track record of hitting or exceeding quota in a SaaS or consultative services environment. Experience selling into Marketing and/or Sales teams is highly preferred —you understand how these buyers think and what earns their trust.
• Experience selling on LinkedIn (posting on LinkedIn for views, direct messaging on LinkedIn for prospecting, outreach, discovery to land demo calls) is highly preferred.
• Comfortable operating without a fully built playbook. You can build process, not just follow it — and you see that as an exciting opportunity, not a burden.
• Senior enough to hold your own in the room with VPs, CMOs, and C-suite buyers. You’ve navigated complex sales cycles through ambiguity and multiple stakeholders.
• Collaborative alongside your competitive drive. You’re a team player who wants to win together, and you understand that building the foundation today creates real leverage for tomorrow.
• Resilient, self-directed, and energized by an early-stage environment. The ambiguity of a startup is a feature to you, not a bug.
• A love of closing. It is part of what drives you.

Additional soft skills we really care about:

● Excellence
● Resilience
● Awareness
● Communication skills
● Leadership, Coaching and mentoring, Teamwork