What to Wear

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Startup / SMB

Smart casual is the move. A clean button-down or polo with chinos and clean sneakers or loafers. Skip the tie. You want to look polished but approachable, like someone who fits their culture. When in doubt, check their team photos on LinkedIn.

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Enterprise / Corporate

Business professional all the way. A well-fitted suit (navy or charcoal), crisp dress shirt, and polished shoes. You are selling yourself the same way you will sell to their enterprise clients. First impressions matter, and you want to look like a trusted advisor.

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D2D / Field Sales

Branded polo or a clean, fitted company shirt with khakis or joggers and comfortable shoes. Keep it clean and professional but practical since you will be on your feet. Avoid anything too dressy. If the company has branded gear, wear it to the interview.

Questions to Ask THEM

"What does your top performer do differently than everyone else?"

Reveals whether they have a clear understanding of what success looks like and whether the role has a realistic path to top performance. If they struggle to answer, it may mean they lack structure.

"What's the average ramp time for new hires in this role?"

Shows how much support and training you will receive. A company with a clear ramp plan (30/60/90 days) is usually more organized. Vague answers might mean a "sink or swim" environment.

"How is quota set, and what percentage of the team is hitting it?"

This is critical. If fewer than 40% of reps hit quota, the quota may be unrealistic, the territory assignments may be unfair, or the product-market fit may be off. Aim for companies where 50-70% of reps are at or above quota.

"What's the biggest challenge the sales team is facing right now?"

Tests whether the hiring manager is honest and self-aware. Every team has challenges. If they say "nothing," that is a red flag. A good answer shows they are actively working to improve and you can be part of the solution.

"Can you walk me through the sales tech stack?"

Reveals how much the company invests in enabling their reps. A modern stack (Salesforce/HubSpot, Outreach/Salesloft, Gong, LinkedIn Sales Nav) means they care about efficiency and data. Minimal tools may signal under-investment.

"What happened to the person who had this role before?"

Tells you whether the role is a growth opportunity (promoted or new headcount) or a revolving door. If the last three people left within a year, ask more questions about management style and expectations.

"How does the company handle territory and account assignments?"

Territory is everything in sales. Understanding how accounts are distributed helps you gauge fairness and opportunity. Watch for favoritism or constantly changing rules, which tank morale and performance.

"What does career progression look like for someone who crushes it in this role?"

Shows if they invest in developing their people. Strong answers include specific timelines and examples ("Our last two SDRs promoted to AE within 14 months"). Vague answers suggest limited growth opportunities.

Red Flags to Watch For

Unrealistic OTE promises

If the OTE sounds too good to be true (e.g., "$200K first year" for an SDR role), dig into the base-to-variable split and ask what percentage of reps actually hit OTE. Inflated numbers attract candidates but lead to high turnover.

No clear sales process

If they cannot articulate their sales methodology or stages, you will be building the plane while flying it. Some reps thrive in that chaos, but most perform better with a defined playbook and enablement resources.

High turnover they will not explain

If the team has churned through multiple reps in the same role, ask why directly. A good company will be transparent. If they dodge the question, that silence tells you everything you need to know.

Quota set before you start

If they expect full quota from day one with no ramp period, the comp plan is designed to save money on new hires, not set them up for success. A fair ramp is 2-4 months minimum for most sales roles.

Manager cannot explain coaching style

Your direct manager has the single biggest impact on your success. If they cannot clearly articulate how they coach reps, run weekly one-on-ones, or develop talent, you will likely be on your own.

They pressure you to accept immediately

A company that will not give you 48-72 hours to evaluate an offer is using the same high-pressure tactics their reps probably resent. Good companies respect your decision-making process because they want committed hires.

Salary Negotiation Tips

Know your market rate before the conversation

Research OTE ranges on Glassdoor, Levels.fyi, RepVue, and Bravado for the specific role, industry, and market. Know the base-to-variable split that is standard (usually 50/50 for AEs, 60/40 or 70/30 for SDRs). When you cite data, you negotiate from a position of knowledge, not emotion. Say "Based on my research, AEs in this market with my experience typically earn $120-140K OTE."

Negotiate base salary, not just OTE

OTE is a target, not a guarantee. Push for the highest base salary possible because that is the money you can count on. A $10K increase in base over 3 years at the company is $30K in guaranteed earnings. If they cannot budge on base, negotiate a signing bonus, guaranteed first-quarter commission, or a shorter ramp with protected draws.

Ask about accelerators and uncapped commission

The best comp plans reward overperformance. Ask what happens when you hit 120%, 150%, or 200% of quota. Companies with accelerators (e.g., 1.5x or 2x commission rate above quota) attract and retain top performers. If the plan is capped, that is a signal they do not want to pay for outsized results, and your best reps will leave.

Get the comp plan in writing before you sign

Never accept a role without seeing the full commission plan document. Verbal promises about comp are meaningless. Review the details: quota, commission rate, accelerators, clawbacks, payment schedule, territory rules, and what happens during ramp. If they say "We are still finalizing the comp plan," that is a major red flag.

Negotiate beyond money

If they are firm on salary, negotiate other high-value items: equity or stock options, extra PTO days, a professional development budget, home office stipend, better territory assignment, or a title bump. A Senior AE title versus AE can be worth tens of thousands on your next job. Also consider asking for a 6-month performance review with a guaranteed raise discussion tied to hitting milestones.

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