* Lack of Relevant Experience: It’s concerning if a candidate's resume lacks relevant sales experience or is not tailored in a way to showcase how their experience is relevant to the open role. Including a personalized cover letter or tailoring the summary/objective of the resume to highlight relevant skills and achievements is important to show alignment. * Inconsistent Job History: A history of short tenures at previous companies can raise concerns about a candidate's commitment and reliability. Aim to demonstrate stability and longevity in your roles, and be prepared to explain any job changes or gaps in employment during interviews. Additionally, always make sure that your resume aligns with the roles on your LinkedIn profile. It’s not a good sign when either the resume or LinkedIn is inaccurate. It’s surprising how often we see misalignment. * Not closing the interviewer: When it comes to a sales interview, not being prepared to ask for the next step in the process or get buy-in on their candidacy is a huge miss. As a sales professional in a sales interview, you are expected to close. It shows you investment in the role and your ability to move a conversation forward. * Skipping thank you notes: It may seem a bit old school, but the best reps I’ve ever hired have all written extremely thoughtful thank you messages during the interview process. Take the time to reiterate your interest in the role and thank the interviewer for their time and insights. It’s a sign of strong follow up and rapport building skills and can further set you apart from the candidate pool.

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.

This is such a great question! Having been a sales professional since 2013, I completely understand how burnout can arise, especially with the constant "reset" every quarter. What’s helped me is creating clear personal boundaries with work and sticking to a structured, repeatable process. By focusing on the things I can control and holding myself accountable to weekly, monthly, and quarterly KPIs, I’ve built a more predictable and manageable workflow. I view sales as running my own business—it requires exceptional time management and operational efficiency.

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"

Build relationships and solve problems. Politics will happen naturally and you can decide your comfortability or desire but I'm a firm believer that if you focus on solving problems, sharing your work, being authentically you and advocating for yourself when you've done those things then "aligning yourself" to "gain momentum" will happen naturally.

Good OKRs define the output you are looking to achieve. Be clear in your outcome and give your sellers the space to define their process. Your managers can lean in on process suggestions, if they need help there. It can be easy to focus on effort metrics like volume of calls or emails, however if the true goal is simply the weekly PipeGen that was achieved or amount of revenue that was booked, use them as your North Star. For roles where they also act as Post-Sales/Success, instead of monitoring meetings, you may want to hold the team accountable to product activation, usage milestones, or active users.

As a sales leader, certain hard skills are essential to drive success, while others can give you an edge but are not necessarily mandatory. Here’s a breakdown of the must-haves and nice-to-haves: Must-Have Hard Skills: 1. Sales Strategy Development • Ability to design, execute, and adjust sales strategies based on data, market conditions, and business objectives. A sales leader must know how to create effective go-to-market plans and align them with the company’s overall goals. 2. CRM & Sales Tools Mastery • Proficiency in Customer Relationship Management (CRM) tools like Freshworks CRM, Salesforce, or HubSpot is crucial. You should be able to analyze pipelines, track performance metrics, and optimize sales processes using these tools. 3. Data Analysis & Reporting • Sales leaders need strong analytical skills to interpret sales data, identify trends, and make data-driven decisions. This includes creating reports on sales performance, forecasting, and setting quotas based on historical data and market analysis. 4. Forecasting & Budgeting • Accurate forecasting of revenue, setting realistic targets, and managing budgets are critical responsibilities. Sales leaders need to project future sales based on pipeline data and market conditions, while keeping an eye on financial performance. 5. Negotiation & Closing Techniques • Sales leaders must have advanced negotiation skills, understanding how to navigate complex deals, and mentor their teams on closing strategies for high-value deals. 6. Market & Competitive Analysis • Strong knowledge of the market landscape, competitor activities, and industry trends is essential to position the product effectively and stay ahead of the competition. 7. Sales Process Optimization • Understanding and improving the sales process is key. This includes implementing best practices for prospecting, lead nurturing, and deal closing to enhance efficiency across the team. 8. Product & Industry Expertise • A deep understanding of the product or service being sold and the industry in which the company operates is crucial. This allows leaders to better coach their team and ensure they can articulate value to customers effectively. Nice-to-Have Hard Skills: 1. Technical Knowledge (e.g., SaaS or Enterprise Solutions) • Depending on the industry, technical knowledge of the product, such as understanding software or cloud solutions in SaaS sales, can be valuable but not always necessary. Having this knowledge can help bridge gaps between sales and product teams. 2. Digital Marketing & Social Selling • Familiarity with digital marketing tactics (SEO, content marketing, paid advertising) and social selling on platforms like LinkedIn can help sales leaders align closely with marketing efforts and empower reps to generate leads more effectively. 3. Sales Enablement Tools & Automation • Knowing how to implement and utilize sales enablement tools (like content management systems, email automation, and AI-powered sales platforms) can boost team productivity and improve alignment with other departments, such as marketing. 4. Customer Success & Retention Tactics • Understanding customer success strategies can help sales leaders focus on long-term relationships and retention, which is increasingly important in subscription-based business models like SaaS. 5. Cross-Functional Collaboration • While not always a hard skill in the traditional sense, the ability to work closely with product, marketing, and customer success teams is crucial for driving sales alignment and organizational success. A familiarity with tools like Slack or project management software (e.g., Trello, Asana) can support this collaboration. 6. Business Development & Partnership Building • Sales leaders who understand how to create and manage partnerships or business development efforts can bring new revenue streams into the business. This is especially helpful for companies looking to expand into new markets or verticals. 7. Sales Training & Coaching • Being adept at designing and delivering sales training programs is a great skill for sales leaders who want to continuously improve their team’s performance. This includes understanding adult learning principles and creating actionable coaching plans. Conclusion: • Must-Haves: Skills like sales strategy, CRM mastery, data analysis, and process optimization are essential for a sales leader to drive and manage a team effectively. • Nice-to-Haves: Skills like technical expertise, sales enablement tools, and digital marketing can provide an extra edge, especially in tech-driven or fast-evolving markets. Mastering these must-have hard skills while building on the nice-to-have skills will ensure a sales leader’s success in guiding their team and achieving business goals.

This is an excellent question, though providing a singular, straightforward answer can be challenging. Identifying root causes can range from straightforward to highly complex. Regardless, proficiency in the following areas is essential: * Customer Use Cases: Understanding ROI, persona-specific value, and the broader strategic context. * Value Mapping: If your champion understands the value but hasn't identified the root cause pain your solution addresses, it's your responsibility to reverse engineer this pain point and help align the buyer on how they will sell the solution internally. Sales Cycle Complexity: Understanding the complexity of your sales cycle is crucial. If you're operating within a shorter cycle with early involvement from decision-makers, root cause identification might occur swiftly. However, elevating the conversation to connect the champion's pain point to a broader strategic initiative will be key in securing executive buy-in. In strategic, enterprise cycles, the root cause may be more elusive. You'll need a plan to identify the people, processes, and work streams your solution enables or optimizes. The good news is that an enterprise strategic cycle is essentially a series of smaller cycles managed with a champion over an extended period. The following context will still apply, but understand that in a strategic cycle, you're always "on" and need to be hyper-aware of moving all evaluating parties through each step. This can be challenging if you're not accustomed to creating professional pressure. When pursuing root cause discovery in either scenario, consider the following: Uncovering Strategic Initiatives: To help your champion elevate the problem to align with organizational priorities, consider the following approaches: * Understand Executive Priorities: Ask your champion what their senior leadership cares about. If strategic language is absent, this may indicate that your champion lacks the seniority needed to push the purchasing request to the right stakeholders. * Leverage Company Messaging: Ask what is being communicated in company-wide meetings or all-hands sessions. Identify key themes or strategic initiatives that leadership is emphasizing. If the messaging is high-level (e.g., "We need to move faster"), determine who owns that initiative and gather additional context to position your champion's request accordingly. * Collaborate on Strategic Messaging: If your champion is more junior, you may need to brainstorm strategic root causes or initiative language together. This exercise can help them better communicate the value proposition in a way that resonates with decision-makers, framing the ask within broader strategic objectives. Now that you've aligned with you buyer on the larger strategic initiative, and hopefully aligned on pain. All you're doing is creating sales process that demonstrates the implication of said pain in the abscence of a solution AND the what happens on the other side of a sales process. I call this "selling value day." That is, we are usually spending the majority of our time selling the process, rather than the outcome, or even the pain. But in order to do this, I recommend that you come up with a few ways to standardize things that will help you maintain professional pressure, like: 1. 3 sentence Primary Business Objective statement - this is a succinct set of sentences that helps executives understand/get aligned on the solution presented relative to the "root cause" 2. 3 pillar Value slide - this is a pillar based representation of pain statements and desired outcomes each tied to business objective and is used to create some dimensionality to the previous Primary business objective. 3. From > To slide - If you're trying to create a sense of "pain: where we are" to "value: where we want to be" I recommend that you do a side by side slide that connects, very simply, the current state (1 sentence) and the desired state (1 sentence) PRO TIP: You want very few words on this slide, but lengthy, story telling context that you can elaborate on when presenting this slide later. PRO TIP #2: Best to reference customer stories here as well - bring these to life with real life examples. 4. Simplified Sales Process - Once you've tee'd everything up, you're now going to want to sell them on what they can expect in trade for their time. It's critical we make the process to getting into the desired state, easy. Or at least as easy as is reasonable

Better Together - Collaboration with other departments and Sales Enablement If you have not already started to build out councils with your core heads of department this will allow for set times for you all to meet to collaborate on the enablement priorities and build out RACIs to outline who is responsible during each phase of each project. Below are three steps that can help you start one 1. Meet with all the key department heads that you need to collaborate with to effectively manage or funnel all the information that is required for sales enablement to build strategy and enablement for the field. Explain what your organization is responsible for and how you can partner together 2. Schedule regular cadence with one representative from each group and form your sales enablement governance council - this allows each head of the department to delegate someone to represent that group in any or all projects that require you all to work together. 3. Keep it documented, share the successes, take input and build together The above is the most efficient to build credibility, trust and collaboration with your department heads, remember they will be talking to the sales leaders in other meetings just like you so building your collaboration and trust will help you all partner better together for the benefit of the sales and the organization.

To effectively define the metrics for which you should hold sales accountable, I look at a few things: 1. Understand the "Sales Math" of the business across some core universally applicable SaaS Sales metrics 2. Compare the performance of the top 1/3 AE's against the bottom 1/3 AE's and look for which metrics contribute the most to high performance. 3. Go deep in those categories and correlate the activities top performers do differently to achieve these results. Quantify these activities to define supporting metrics which will lead to success. To break this down, let's understand the foundational "Sales Math." This is the equation to hit quota. The equation is fairly simple, but everyone's vernacular is different. It is actually extremely important to have very well defined steps in the equation to get consistency across your entire team. For example, we use opportunity stages with clear exit criteria for the buyer & seller to provide consistent insight into our Sales Math. So I would actually use a Stage 1 Opp Created - instead of Discovery Call, and Stage 3 Opp instead of Demo. For the purposes of this article, I'll use general sales terms that each business should be able to use as a starting point and customize from there. Here are the metrics that go into the Sales Math equation: * Activities to create a Discovery Call * # Discovery Calls per quarter * # Demos per quarter * Discovery Call to Demo conversion ratio * # Closed Won Deals per quarter * Demo to Closed Won conversion ratio * Average Deal Size * Average Deal Cycle These metrics will allow you to create the math to hit quota. If the current team's metrics do not consistently lead to the results you're looking for, then the Sales Math may be aspirational. If your team is executing against plan, then this may be your actual current metrics. Regardless, this is what you should feel confident telling AE's is the realistic, attainable and surpassable way to hit quota. For example, it could look like: $250k Quarterly Quota Average Deal Size of $84k 3 Deals to hit quota Close ratio of 33% 9 Demos needed per quarter 60% conversion ratio of Disco to Demo 15 Discovery Calls needed per quarter 50 Activities to create a Disco 750 Activities needed per quarter* *one note on activity. It's a metric I'll always track to understand a baseline level of effort, but I will often leave this out of the Sales Math when dealing with higher complexity sales and more senior AE's. Up to you if this should be in your Sales Math equation. Now take your Sales Math, and map your high performers against your low performers to look for which metrics have a high correlation with success. This exercise can be extremely surprising, so be open to what the data shows you, and hold your strong opinions loosely. Let's extrapolate this exercise across two different scenarios: Scenario 1 - Enterprise Here's how the exercise played out when running it against a more enterprise business (numbers are directional): 1. Activity, Discovery Calls and Demos were almost identical across high & low performers. This told me that pushing "more activity" was only going to have so much impact on performance. 2. The Closed Won conversion of top performers was 46% vs. 25% for the low performers. This was a huge gap, and had major implications on the Sales Math. 3. The Average Deal Size of top performers was $160k vs. $70k for low performers. This is also a huge gap compounded the success or struggles of each group when combined with the stat above. So the key metrics to optimize were Average Deal Size and Demo to Close Ratio. We wanted to maintain our activity levels, but really lean into increasing ADS and strategies to help with Deal Execution. Based on this knowledge of what would have the biggest impact in high performance vs. low performance, we added in some metrics & activities that would contribute to these results: * Updated our account prioritization to ensure a focus on the top deals & tracked activity against Priority 1 accounts * We blocked off time each week to prospect into our top accounts & scheduled strategy sessions to help get more meetings with these accounts * We tracked # of Discos with P1 accounts * # of Demo's with $100k+ Opportunities For Deal Execution * We tracked multi-threading in each account * Have we made an executive connection? * We created a cross-functional meeting to lean into competitive differentiation strategy * We set a threshold for accounts that needed a key deal review & updated our process to improve efficiency and make room for more accounts reviewed each week. Scenario 2 - Transactional Here's how the exercise played out when running it against a more transactional business (numbers are directional): 1. There were two camps of high performers. Those with extremely high activity, and those with higher disco to demo efficiency. Our most consistent top performer was a combination of both. Low performers fell into a similar pattern of either low activity or low conversion of discos to demos. 2. Deal size and win rate didn't have dramatic differences outside of 1 AE who closed the largest deal in segment history. This wasn't repeatable so we eliminated that result instead of putting too much time in hunting whales. 3. Average Deal Cycle for top performers was 39 days vs. 52 days for lower performers. Top AE's were closing deals faster, which allowed for more time to close more deals. From this data we defined additional metrics and activities to drive better results: * Upped the baseline activity volume expectations - there is a diminishing point of returns, but higher volume was almost always a component of success. We raised the bar, but also coached our highest volume AE's to lean more into their efficiency metrics instead of pushing to just do more. * Managers went deep on quality of discovery calls coming into the funnel * Title & Seniority level of Prospects - lower conversion was correlated with lower titles. * Was the company in our Ideal Customer Profile? Quality of company greatly impacted conversion * Why now? Did we offer someone a gift card or just bug them until their defense was worn down? Or was this call predicated on funding, a new hire, an inflection point in the business, intent or some other business catalyst? * Managers inspected quality of prospecting messages * Managers inspected quality of discovery calls * We rallied around creative promos to help the team close deals faster * We replicated decks top AE's were using to build value and establish trust faster In both Scenario 1 and 2 - we started with the baseline Sales Math, and through comparison of top performers vs. low performers we were able to lean into the 2 key metrics that had an outsized impact on performance. We then defined key activities and additional metrics which we could hold the team accountable to, that we knew would correlate towards greater success across the team. How easy was that? :)