In order to get a better understanding of what you could be walking into, I suggest asking the question "What is your biggest problem and can I help solve it?" It shows genuine interest in the interviewer's pains/goals and enables you to see how you can make an impact. Aside from this key question, always make sure to check out these resources before stepping into the interview. 1. Company Website: Familiarize yourself with the company's products or services, mission, values, financials and recent announcements. 2. LinkedIn: Research the hiring manager and other key stakeholders to gain insights into their backgrounds and professional interests. 3. Glassdoor or RepVue: Read reviews from current or former employees to learn about the company culture, interview process, and potential interview questions.

Theory provides the groundwork and techniques in an ideal setting, while practice applies these concepts to the unpredictable real world, especially in fields like sales. To bridge theory with real-world experience, break down classroom-taught skills into practical applications for daily interactions. What is the skill that's being taught in the classroom and where else can it be used, outside of the sales process? Negotiation, executive presence, conducting discovery, etc. are all skills that can be applied to other ares of work/life. Where and how can you provide an opportunity to practice building this skill besides with your customer? Then, consider the amount of effort/scale the skill can be practiced to gain more experience: * Large scale/low touch: Use tools like AI simulations and roleplays for controlled practice. This is best leveraged when learning a new framework or skill. * Med scale/touch: Offer chances for individuals to apply skills in internal meetings and conversations where the skill can be demonstrated with others in a safe space. * One-to One/high touch: Encourage leaders/trainers to provide feedback through reviews of recorded calls or shadowing in-person meetings for timely coaching to the individual and the skill.

Let me answer this from the perspective of one of my key cross-functional partners—Product Marketing (PMM). When we first sit down with PMM teams, they usually have a lot of information they think will be helpful for sellers regarding a new product launch or initiative. However, much of it tends to be 'fluff'—nice-to-have details that often overshadow what sellers actually need. I always ask PMM to think like our sales teams and focus on two key questions: 1. "What's in it for the seller?"—Essentially, how can sellers make money? 2. "What's in it for the customer?"—How can sellers use this to make money? If their content doesn't answer these questions, it’s likely just noise. At the end of the day, content creators want their work to be consumed, and helping cross-functional teams understand this sales-focused perspective ensures that everyone wins.

I stole the idea of “WGLL” from Kevin Dorsey, who works across his leadership structure in sales teams to be maniacally focused on what good looks like, and work backwards from there. As such, I’ve rooted our metrics in support of WGLL - not from the perspective of “Amy & Bobby are the best, let’s have everyone do what they’re doing!”, but rather in using WGLL activities across my sales leaders to understand specific wins from the sales funnel and the supported customer experience to drive those metrics of success. For an example: we found that Amy is delivering a lot of value in the on-sites she’s running in her territory, let’s equip the team with her model (How far out she schedules, targeted personas, decks + sequences to set the meeting) and then hold them accountable to a number that Amy has driven to: 2 on-site meetings per month. Bobby is doing fantastic work top of funnel, and so we’ll capture what personas he’s engaging, what content and sequences he’s sharing, and communicate that as the KPI to the rest of the team.

To be successful in sales going forward, professionals need a mix of both soft and hard skills. Here are the most important ones to focus on: Soft Skills: 1. Emotional Intelligence (EQ): • Understanding customer emotions, handling objections, and building rapport are critical to gaining trust and maintaining strong relationships. 2. Active Listening: • Listening to what the customer says—and doesn’t say—helps identify their true needs and allows sales reps to tailor solutions effectively. 3. Resilience & Grit: • Sales is full of rejection. The ability to bounce back and maintain a positive attitude in the face of adversity is key to long-term success. 4. Adaptability: • The market, customer demands, and technologies are constantly changing. Sales professionals need to be flexible and able to pivot quickly. 5. Effective Communication: • Clear, concise, and persuasive communication, both written and verbal, is essential to conveying value propositions, closing deals, and maintaining client relationships. 6. Problem-Solving: • Customers are looking for solutions to their pain points. Being able to identify problems and provide tailored solutions separates top performers from the rest. 7. Collaboration & Teamwork: • Sales is increasingly collaborative, requiring coordination with marketing, product teams, and customer success. Building strong internal relationships helps sales professionals deliver better results. Hard Skills: 1. CRM Mastery: • Knowing how to efficiently use Customer Relationship Management (CRM) tools like Freshworks CRM for tracking leads, managing pipelines, and analyzing sales data is critical for sales effectiveness. 2. Data-Driven Decision Making: • Sales teams now rely heavily on data to inform their strategies. Sales professionals must be comfortable interpreting analytics and using data to drive decisions and forecast accurately. 3. Sales Automation & Technology Tools: • Familiarity with sales automation tools, email marketing platforms, and lead-generation software helps streamline workflows and increase efficiency. 4. Product Knowledge: • Deep understanding of the product or service you’re selling is essential. This enables you to articulate its value, answer technical questions, and position it against competitors. 5. Negotiation Skills: • The ability to navigate complex negotiations and find win-win solutions is a crucial skill for closing larger, more complicated deals. 6. Social Selling & Digital Presence: • The ability to use platforms like LinkedIn and other social networks to engage prospects, build personal brands, and generate leads is becoming increasingly important in modern sales. 7. Market & Industry Knowledge: • Understanding the broader industry landscape, competitors, and trends helps sales reps anticipate changes and position their products more effectively. Conclusion: • Soft skills such as emotional intelligence, communication, and resilience will help sales professionals build relationships and navigate challenges. • Hard skills like CRM proficiency, data analysis, and product knowledge ensure they can operate effectively and strategically. Balancing and developing these skills will help sales professionals succeed in an evolving sales environment.

This one’s easy! In sales, your performance metrics are your best evidence. Start with your revenue numbers—they’re the clearest indicator of success. Beyond that, track and showcase your quarter-over-quarter (QoQ) improvements in metrics like close ratio, deal size, or pipeline growth. For example, demonstrating consistent improvement in your ability to close deals is a strong justification for a salary increase. Tracking your own metrics not only helps you improve as a sales professional but also shows leadership you’re thinking strategically and providing valuable insights to the business. Thus making the business ant to invest in you further.

You have to have a glutton for punishment moving from structure to no structure, take it from me, but it can be such a rewarding and fulfilling experience to build something from 0→1. Throughout my career, I wouldn’t say there have been many surprises, moreso ‘opportunities’ to put a positive spin on it. Systems & Reporting: We forget how easy we have it being at a larger organization where you have countless resources for technologies that have already been vetted and rolled out, and full funnel reporting to support pipeline/revenue trends, forecasting predictability, etc. * My advice for any revenue leader starting from scratch is to bring in a RevOps hire. This is the most critical investment you can make to build the foundation for your revenue motion. Market Positioning & Value Prop: Don’t expect a clear deck with clear customer case studies, ROI metrics, customer facing collateral, competitive positioning, discovery questions, pitch scripts, etc. As the first sales hire, you must build this. * My advice: Customer tour of duty. This is your opportunity to connect with customers to understand how they use your product, what’s resonating, what needs improvement, etc. Pipeline: You likely won’t have a marketing engine generating inbound leads, let alone an outbound engine targeting key accounts that have high propensity to engage with you. * My advice: Partner with RevOps to understand your target audience by: * Defining your ICP: company size, industry, revenue, geographic location, and technology stack * Leveraging Data: CRM, historical deals, and win/loss analysis, inbound analysis, etc. to find patterns in successful accounts * Intent & Firmographic Data: Third-party tools to gather intent signals (hiring, tech stack, funding, ICP profiles, etc.) and firmographic information (company size, geo, industry, etc.) Hiring: Do not rush this. As the first sales hire, you should be running every single deal for the first 30-60 days. Deeply understand your customers, their challenges, and how you can solve them. * My advice: You must fire “Full Stack AEs” who have something to prove and are willing to hunt, convert, close, and expand. Bring on talent who can do it all. Less is more and remember to hire for the innate skillsets that you cannot teach: grit, humility, curiosity, high EQ, perseverance, hunger, etc. Product & GTM Alignment: This is one of the most critical relationships to get right if you want to grow your revenue engine. * My advice: Create a shared vision with Product and how you plan to differentiate in the market. Create a consistent and clear feedback loop between you and your revenue team and Product where you sync often to understand which key features, workflows, and customer requests would impact the most ARR if rolled out. Communication is key, but ensuring you cut out the noise from one off feature requests is most important. Decisions should be made in a binary and objective approach (ARR).

There is a give and take with standardizing KPIs but also having enough variance to account for things segment, (Strat, Ent, MM, Growth) number of accounts, and so on. The easiest way to have consistency and also provide a lens to inspect forecast is by implementing standardization when possible. No matter what segment you're in or how many accounts you have, if a deal is 345 days old... that's going to tell me something about the forecast accuracy of the stage it's in. I am a big fan of ensuring reps are training that in the mid point of the quarter or month, whatever your quota and cadence is, deals with a close date in quarter or in month must be in Best Case, Commit, or Closed. Nothing can be in "Pipeline" or "Omitted"

Be clear on your goals and show progress against those week over week. Use that to show the quality of work being done and then be specific on where you're running up against challenges in achieving that plan where more resources can help. Important to show you've thought threw alternative options particularly where there are resource constraints.

Customer feedback and insights from discovery serves as the foundation for the business case that will support your deal. Ultimately, the business case is "the story that is being told when you are not in the room" - this means whatever story your prospective customer has crafted based on your conversations, articulated product value proposition, and data/details to support their needs is the narrative they're using to build a case to buy internally. Your job is to leverage what you were able to uncover from your discovery to help your prospective customer tell that story in the best way possible without you being there. The main aspects you'll want to uncover to help them craft that story is: * Why Do Anything? what is the cause for change? * Why Now? what is the urgency for them to do it now vs. in the future? * Why Your Solution? compared to every possible solution, why is your solution uniquely the best? Without a business case, you do not have a deal. However, with a strong business case narrative built from deep discovery, you can expedite your sales process and strengthen your deal, so take those insight you learned from discovery and co-create with your prospect their business case narrative in their own words.