One of my favorite sales interview questions to ask is "Tell me about a time something did not go according to plan in your personal or professional life. What happened and what would you do differently, if anything?" This one's great because it helps the interviewer see if the interviewee is just as comfortable talking about their failures as they are about their successes. It allows the interviewer to see how the person handles setbacks, what they do when setbacks occur and what their overall ability to handle unexpected curveballs is like. The best answers are usually authentic, vulnerable and showcase a growth/abundant mindset. Abundant mindsets allow people to see setbacks as opportunities for further improvement rather than limitations. 

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.

I often hear a few common concerns from enterprise prospects. These usually revolve around worries about the price, potential risks, getting locked into a single vendor, and status-quo objections. Cost Worries: When prospects bring up cost concerns, I like to highlight the value our solutions bring. I show them how our offerings are designed to solve specific issues and bring tangible returns. Plus, I work closely with our financial experts to offer flexible pricing options and demonstrate the long-term benefits of their investment. Mitigating Risks: It's only natural for enterprises to be cautious about adopting new tech. To address this, I point to our track record of successful implementations, backed by glowing customer testimonials and case studies. I also stress how adaptable and scalable our solutions are, fitting seamlessly into their existing setup and future growth plans. Avoiding Vendor Lock-In: Some prospects worry about being stuck with a single vendor for the long haul. I reassure them by emphasizing our focus on interoperability and open standards. I highlight our wide range of integrations and partnerships, underlining the flexibility and freedom our solutions offer. This way, they know they can integrate with other platforms and technologies if they need to. Validating with Proofs of Concept: Given our emphasis on proofs of concept aligned with the customer's future goals, prospects often want to see real results. I suggest starting with a smaller pilot project or proof of concept that's tailored to their specific needs. This hands-on experience helps build trust and confidence in our solutions, often leading to broader adoption. By addressing these concerns with a mix of personalized value propositions, strong case studies, and adaptable implementation strategies, we can show how our solutions align with the prospect's big picture vision while easing worries about cost, risk, and vendor lock-in. This approach ensures that our tactical opportunities lead to long-term, mutually beneficial partnerships with our enterprise customers. Status Quo Resistance: Another common objection we encounter is a hesitancy to disrupt the status quo. Many enterprise prospects are comfortable with their current processes and systems, even if they may not be fully effective. To tackle this, I approach it as an opportunity for growth and improvement. I share success stories of similar organizations that made the leap from their familiar routines to our solutions, showcasing the positive impact it had on their operations. By highlighting the potential for transformative change, we can overcome the inertia associated with maintaining the status quo and inspire prospects to embrace innovative solutions aligned with their strategic vision. This approach empowers them to envision a future state that not only meets their immediate needs but also positions them for long-term success. By addressing these concerns with a mix of personalized value propositions, strong case studies, and adaptable implementation strategies, we can show how our solutions align with the prospect's big picture vision while easing objections about cost, risk, vendor lock-in, and status quo resistance. This approach ensures that our tactical opportunities lead to long-term, mutually beneficial partnerships with our enterprise customers.

Coming into an organization as the first sales hire puts a lot of responsibility on your shoulders. You are basically in charge of proving the validity of this function within the company. There are a few things that I would consider and act on in this position: Start with the short term. As a first hire in a sales organization, you are required to deliver results that have a very immediate impact that meets the business needs. This means focusing on some low-hanging fruits in order to deliver results within a short time frame. Build a framework. As a first hire within the team, you should make sure you document your work, and create clear guidelines and processes, with the expectation of adding additional members to the team in the future. This will ensure a smooth expansion of the team while positioning you as a thought leader and a pivotal member of this function. Go beyond your scope. As a junior sales hire, never underestimate the power of tenacity. I always invite my team members to push the boundaries and look for additional scope and responsibilities whenever they feel capable. This is a very strong signal that you are willing to take on more, and when management will face a new task at hand, they will know they can count on you.

I really like this question because it's so true! Leadership can break a lot of trust by implementing incorrect KPIs for a segment. Experienced sellers will get angry they are treated like SDRs, etc. The best thing leaders can do is watch, listen, observe, and then replicate. What have the most successful reps done in this position? Are they having 10 calls a week, 2 on-sites a month, and 1 "high value activity" a quarter (like exec intro, hackathon, etc)? Standardize from the top and make excellence the norm.

Moving up-market is no easy task. It adds a great deal of complexity, precision, and requires more people, processes, workflows, and technologies to do it effectively. This initiative must be done company wide and has to address the ongoing challenges that your target (or evolving/new target) audience must solve at a global scale. Here are a few things you’ll need to think about as you shift from a velocity to a transformation motion: 1. Historical success 1. Have you closed up market in the past? 1. Can you create a playbook around these successes? 2. What deals have we lost up market? Can we take learnings from these losses in order to adjust our sales motion, product, security, legal, etc. in order to win? 2. Product 1. Are you solving an enterprise need? 2. Are you sustainable for an enterprise wide deployment? Have you done this in the past? 3. Integrations and workflows 4. How do you differentiate in the competitive market? 3. Security 1. Configuration and posture management 2. Architecture 3. Monitoring and threat protection 4. Automated workflows 5. DevSecOps 1. SSO, SAML, authentication flows 6. Governance and risk compliance 7. System functionality and APIs 4. Marketing and Sales alignment 1. Target audience 1. Does this change as you go up market? 2. Target account list 1. Firmographic + technographic data 3. Segmentation 2. ABM (account based marketing) 3. Lean on your investors for support and guidance 4. Do you have the technologies to support this transition at scale? 5. Customer support 1. What are the needs of your current Enterprise customers? 1. How will you scale in order to support more? 6. Revenue streams 1. Top down - ICP, key targeted accounts, ABM/pure outbound 2. PLG - Free, bottoms up, pilot + PoC process 3. Community Led - Empower people to become an extension of your brand, product feedback, customer advocacy, resellers, consultants (creating additional revenue streams)

I stronly believe that sales people are one of the most likely people to get to the highest position in any business right upto the role of a CEO. In fact, many CEOs in global companies either come from either sales or product background. * A sales person would start their sales career somewhere as a SDR/BDR. * And then move into an account executive quota carrying role. * From there, they would either branch into management or continue to be a senior Individual Contributor (think about a Key Account Director) * I have seen successful sales people eventually getting into GM, CRO or even CEO roles

In my experience, communicating the performance & progress of your sales team to the company helps to connect all employees to the mission. It can create transparency into the health of the business, aligns individuals within the company more closely to the voice of the customer, and enables you to more easily activate resources when support is needed. On a Daily Basis... * Every time a deal is Closed/Won, a "Congratulations" email is sent out to the whole company, and a Slack message is posted in our "team" channel sharing the details of the deal & the "Win Notes" (ex. the customer, the value of the deal, the "why" behind their purchase, any learnings, and shout-outs to teammates who helped to close the deal) * For the biggest deals or most special wins, I'll also create fun memes showcasing the rep & the customer and share that via Slack & email too On a Weekly Basis... * I'll create a Freehand with 4-5 slides sharing our progress (Closed/Won against Target, Pipeline Generation over the last week, etc.), shouting out the biggest & most prominent deals of the week, and sharing the most relevant & interesting customer stories. Then I'll record a 3-4 minute video walking through the content, adding my commentary & perspective, and then I'll share the video & the Freehand in our "team" Slack channel so everyone in the company can watch it & engage with the content * I also look for opportunities and encourage my sales managers & sales reps to post in our "sales" Slack channel any interesting stories or learnings throughout the week. Sharing snippets from chorus calls, best practices for generating conversations or overcoming objections, and capturing the greatest success stories helps to raise the overall knowledge of the organization. On a Monthly Basis... * During our company All-Hands, I'll provide and expanded version of my weekly Freehand & video, and also look to provide the platform for 2-3 of our sales reps partnered with their account or customer success managers across different segments/regions to share their customer stories with the entire company. And keep in mind...it's as important to celebrate the journey just as much as the wins, especially if you're in an earlier stage organization. Communicating the behaviors, the mistakes, the learnings, and the process behind your sales motion is often even more valuable for your entire organization than the wins alone.

Be prepared: C-Suite folks are busy people- don't waste their time. Ensure you are prepared for every meeting you have with them. Anticipate the questions you would expect them to ask and have your answers ready to reply with in real time. Be clear and concise: It goes a long way in terms of how you show up to the C-Suite if you can articulate what you need to say in a clear and concise way. If you are taking the time to prepare, this should be easy enough to accomplish. Properly prepare them: If you are running a meeting or call together or simply need your C-Suite's involvement in a deal or project you're working on, it is critical to properly prep them for it. Take the extra time to build out a pre-read that outlines the background of the deal or project, who's involved, the goal of their involvement, what you actually need from them, and in some cases suggested ghost written content (i.e. ghost written email in a deal for exec to exec alignment). Simply put, if you are asking something of them, make it as easy as possible for them to get up to speed and execute on it. Be confident: The C-Suite are people too! Of course, have respect, but also have confidence in you and make sure that shines through. 

Sales KPIs play a critical role in forecast accuracy, especially in unpredictable markets. Amidst the market turbulence, really the only thing you have are deal execution and forecast accuracy. The difference between having a math based forecast everyone is aligned around vs not is stark. There are so many ways to cut your forecast in an effort to determine where you'll land. The math itself is important but the most important is having a shared language and "walkup" in order to pinpoint the assumptions you're making - so you can have an in-depth discussion in a short amount of time.