Must-Have Sales Leader Hard Skills: * Data Analysis and Decision Making * Decisions can't be made on a whim-they need to be based on data * You need to be able to analyze data to understand the health of your business and the businesses of those who report to you * You need to be able to pull key insights from data to drive strategy and as a way to get your team bought into executing on the strategy you set * Communication Skills * With customers, other leaders, cross-functional partners, and reps * You need to be comfortable having tough conversations when necessary * You need to inspire your team to take action and execute * Time Management * Time is limited- you need to understand how to maximize it, free it up (delegate), and prioritize/deprioritize * Negotiation Skills * Not just with customers, but internally with cross functional partners and key stakeholders in order to get things accomplished within the business

Sales stakeholders can come from any department within an organization and as the company grows, their input is key to sales success. A few examples may be: 1. Product Teams: aligning sales strategies with new offerings and/or customer feedback 2. Marketing: greater integration for cohesive messaging and lead gen 3. Customer success: ensuring client satisfaction and retention 4. External partners: distributors, resellers, support partners can help expand market reach The best method to building and maintaining relationships with your stakeholders is to regularly communicate with them. Show appreciation for their support, inform them of changes, address their concerns and involve them in key decisions that may impact their area of the business. Creating trust and consistent communication will help build, or strengthen, your relationships.

I think there’s a lot to be said about optimizing sales processes with AI. As software continues to improve this will allow AEs to be more productive, manage larger books of business, and deliver highly customized outbound messaging. That said, given the sheer volume of outreach prospects receive today, it’s more important than ever to differentiate yourself, build your network, and establish yourself as a thought leader in your space. If I were an AE starting today, I’d focus on what I want to specialize in and start building relationships—not just with prospects and customers but also with partners in the ecosystem.

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).

Firstly, it is important to recognize that discovery is not one stage of a sales process nor is it only the questioning that occurs on your first meeting. Discovery is a continuous journey of leading with curiosity, probing deeper, summarizing your understanding, and validating your takeaways through the sales process and with each new individual in the sales process. To ensure your discovery is efficient & effective... * Do Your Research & Prepare: the better you prepare for the conversation and align on the answers you need to best identify if/how your solution may be of value to the prospective customer the more effective you'll be able to use your time * Stay Curious: if you engage in curious, open-ended questions you will be able to uncover more critical information than if you focus on a standard set of pre-defined & closed questions * Probe Deeper: don't take just the surface level answer to questions, keep digging deeper to get to the root of their current state, goals, challenges, pain, etc. * Summarize & Validate Your Understanding: always make sure to summarize what you heard and validate you heard that correctly. Ultimately, the underlying business case is your prospective customer's story in their own words, so while you can craft it through discovery, to align on the true narrative, it needs to be in their words. If through your conversations you cannot get the prospective customer to articulate 1) why they need to do anything, 2) why they need to do it now, and 3) why your product is the best solution, then that may indicate you have sufficient holes in your deal which could require you qualifying out.

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"

Effective communication of sales updates and activities is crucial for keeping the entire company aligned and informed. Here’s how I approach it: Utilize Dashboards for Transparency: * Dashboard Review: Well-structured dashboards that track key metrics such as lead volume, outbound activity, and deal progress are essential. While sales teams may not always focus on dashboards independently, reviewing them in a structured setting can be very effective. * Weekly Stand-Ups: During weekly stand-ups, briefly review these dashboards to provide a quick snapshot of current sales activities. This ensures that everyone knows the overall activity levels without spending too much time on details that may not require deep discussion. Focus on Meaningful Sales Activities: * Highlight Key Milestones: Beyond just looking at activity metrics, it’s important to focus on the sales activities that truly matter. This includes tracking the number of deals that have advanced to the next stage and the milestones that have been completed. While this can sometimes be challenging to capture, modern Revenue Operations (RevOps) tools can simplify the process. * Tools for Automation: Tools like Motion, Superhuman, HubSpot, Salesforce, Outreach, and SalesLoft are capable of automatically aggregating key events and milestones within deal cycles. By leveraging these tools, you can ensure that you’re tracking and reporting on the most critical aspects of deal progression. Regular Review in Stand-Ups and One-on-Ones: * Weekly Stand-Ups: In these meetings, review the dashboards and key milestones. This keeps the sales team and the broader organization informed about where things stand and what’s being accomplished. The goal is to keep these reviews focused and actionable. * One-on-Ones: In individual meetings, dig deeper into the details of specific deals or challenges. This is where you can discuss strategies for advancing deals, overcoming obstacles, and refining the sales process. Tailor Communication for Different Audiences: 1. For Executives: Focus on high-level metrics and strategic insights. Highlight how sales activities align with overall business goals and where the team is progressing significantly. 2. For Cross-Functional Teams: Emphasize how sales activities intersect with other departments, such as marketing, product, and customer success. Could you make sure they understand how sales updates impact their work and how they can contribute to advancing deals?

I think any KPI that is not integrated into the quota and comp structure for any AE by and large is misguided. If you want AEs to focus on specific behaviors then build it into their comp plan and prioritize quota relief over increased commission payments if you have to choose. There are only two exceptions to this in my mind: any KPIs (pipe coverage, onsite meetings, etc.) where you can establish a direct connection to the health of those metrics and their ability to close more revenue OR behavior changes you might want to see mid year, in which case you can use SPIFFs as a tool to align incentives to the behavior changes you want to see. And for any behaviors where the KPIs or SPIFFs are not baked into their quota, be sure to have dashboards that accurately reflect what is happening and commit to communicating regularly progress each AE is making against them. They will otherwise be lost or forgotten about as quota relief and commission always reigns supreme.

Many businesses focus on the effectiveness of a seller, where most of the attention should be. However, it can be very important to look at the effectiveness of those supporting your sellers, by measuring AE ramp time. If you can turn a 6 months period into say 4 months, you not only improve your revenue, but you can also improve the AE experience, leading to better employee satisfaction, higher referral rates, and lower attrition.

If I were a sales rep trying to justify a raise, I would ensure I know: -Performance against quota -Percent to goal -MRR / ARR sold -If at a very early stage company, your contribution to the company's growth might be material, what % growth on the top line did you drive? -If larger, I'd be thinking about the KPI impact of strategic projects. I.e. if you developed a sales play that increased close rates of your peers from 20 to 30% - can you quantify that impact in revenue. It's a lot easier to ask for a raise when you can spell out that you drove $1 mil in incremental growth above and beyond your quota.