Training And Development Manager Jobs in Vermont

Nationwide chains, multi-market attraction groups, major tour operators, and national activity brands — recognized names with real revenue behind them, who've never signed with us or aren't live yet. Your job is to change that.

You own new-logo enterprise acquisition for our fastest-growing category: nationwide chains and multi-market operators across Local Activities, Tours & Attractions. You'll find them, pitch them, structure the deal, and close it — often across the table from a founder, VP, or C-suite. Then you'll hand it off clean so it activates on the strategy you sold.

This isn't order-taking off a marketing list. You build the pipeline, you run the cycle end to end, and you're paid on what you actually close and turn on.

• Real deal authority. You carry genuine discretion on pricing, margin, availability, and contract structure within Enterprise guidelines. You decide when to hold the line and when to flex to win — you're not routing every term through three approvals.
• Logos that matter. These are recognized national and multi-market brands. When you close one, it moves the category and it shows.
• Paid on outcomes, not activity. You're incentivized on signed, activated revenue and new accounts. No one's counting your dials. Close well and the comp follows.
• A category on the rise. Things To Do is scaling nationwide and leadership is watching. Your wins — and your read on the market — directly shape where we take the business next.
• Modern tools, real leverage. You'll close faster because you've got AI in your workflow from day one (more on that below). Groupon runs on Claude Cowork and Claude Code, so the grunt work of research and drafting stops eating your selling time.
• Autonomy by design. You run the full cycle solo, build your own playbook when the standard one doesn't fit the account, and own your number without waiting on anyone.

• Run the hunt. Disciplined B2B outreach against a targeted list of high-value nationwide and multi-market prospects — pulled from your own network, your own research, and the lead pipeline.
• Own the full cycle. Source, pitch, negotiate, and close nationwide and multi-market TTD merchants, frequently at the C-suite level.
• Structure the deal. Build and negotiate complex terms — pricing, margin, availability, contract structure — using Enterprise guidelines and your own judgment.
• Sell from insight. Understand each partner's business model, consumer base, competitive position, and profit drivers before you pitch, so you're negotiating from a position of understanding, not guessing.
• Bring the strategy. Present merchants with sharp, tailored proposals and insights that win the deal.
• Hand off clean. Align with Merchant Success on terms and strategy at close so activation keeps the momentum you built — no deals stalling, no renegotiation.
• Know the mechanics. Speak fluently to static, variable, and dynamic pricing, redemption and voucher methodologies, and how offers work across connectivity (Voucher, API), tax, and reconciliation — with support from partner teams. You'll get training; you bring the curiosity to master it.
• Shape the roadmap. Feed industry trends and frontline insight back to Groupon leadership to influence our strategic direction for Things To Do.
• Use AI like a pro. AI fluency is expected from day one. You use AI daily for prospecting, research, and outreach drafting to compress the time from first contact to signed contract — and you can build automations and agents to scale yourself.

Heads up: this role includes 4–6 weeks of paid Chicago travel in your first two months — to set you up for success.

• BS/BA in Business, Sales, or a related field, or equivalent experience.
• 3-5+ years of Enterprise B2B sales experience — Things to Do is the preference. SaaS, digital media, or a fast-moving marketplace also valuable — closing complex, multi-stakeholder deals.
• A track record of hitting or beating New Revenue or Gross Profit and GP% targets, with strong historical close rates on time-to-market-critical (TMC) deals.
• Fluency in deal structuring: margin, contract terms, and the judgment to know when to hold the line and when to flex.
• Familiarity with ticketing / reservation platforms and connectivity APIs.
• Comfort running the full sales cycle solo, from independent research and lead management through close, with minimal oversight.
• A strategic thinker and presenter, and a go-getter, always driving growth and scale.
• Working AI fluency — you use AI tools as a default part of prospecting and deal prep, not an occasional experiment.

• Tenacious, not rigid. You know when flexibility wins the deal. You read the room and pivot to land the story.
• A closer. You treat "no" as a data point, not a stop sign.
• Outcome-driven. You'd rather be measured on revenue than activity.
• Genuinely AI-native. You use AI as a productivity multiplier, not a novelty.
• A builder. When the standard playbook doesn't fit the account, you write your own.

At Groupon, we build on five principles: Extreme Ownership, Speed Over Comfort, Impact Obsessed, Simplify to Scale, and Disciplined. These aren't values on a wall — they're how we show up. In this role:

• Extreme Ownership — Your pipeline, your number. You build your own path to close instead of waiting on marketing-sourced leads.
• Speed Over Comfort — You send the outreach before the deck is perfect. Cold, nationwide accounts don't wait for polish.
• Impact Obsessed — You chase the logos that move GP, not the easy wins that pad activity metrics.
• Simplify to Scale — When a deal structure works on a hard account, you document it so the next rep closes faster.
• Disciplined — Your CRM mirrors reality: stage, next step, follow-up — always current, never optimistic.

• New enterprise TTD logos signed per quarter (nationwide + multi-market), GP-weighted.
• New Gross Profit and GP% delivered against target.
• Close rate on time-to-market-critical (TMC) deals.
• Pipeline conversion from first contact to signed contract.
• Clean handoff rate to Merchant Success — deals that activate on strategy, without renegotiation.

• Base Salary: $66K–$110K + 60% bonus target
• Target OTE: $120-150K+ based on performance
• Full benefits package including Medical, Dental, Vision, EAP, 401(k) Match, ESPP, Life & Disability Insurance, FSAs, and more
• Real impact on a high-visibility category
• Autonomy, ownership, and a real chance to influence how major national brands show up on Groupon