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.

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)

Since nearly everything is quantified in sales, OKR's can sometimes come across as redundant and inconvenient to manage to the uninitiated. But OKR's are an amazing vehicle to drive focus on the core strategic initiatives that will generate greater success, and gain cross-functional alignment, visibility and support in achieving these goals. There are two major benefits IMO opinion in defining Sales OKR's: 1. Clarity - the process of defining Objectives and Key Results, if applied with rigor and assistance from someone truly knowledgeable in the process, can provide immense clarity into what you're looking to achieve and how to achieve it. The question was about the output, but let's not overlook how valuable the process can be to get really crystal clear on the Objectives that will have an outsized impact on team results. 2. Cross-functional alignment - OKR's are a company initiative, not a Sales initiative. This means it's a common language across departments, that can be used to unite teams in a shared mission, and increase visibility in what other departments can do to help each other out in achieving their objectives. There are few other tools that are as impactful as a supporting team attached to one of your KR's having to read out progress each week to their leadership. Every sales person wants more support from the company to sell. If it's possible to define exactly what that support is, who it's from , and tie it to a KR... drumroll please... you just got the support you needed via OKR's! So what defines good Sales OKR's? First step is in accurately defining the highest priority Objectives, that if achieved, would have a greater impact on Sales than anything else this quarter. A couple nuances to address: 1. Typically there are top line company objectives that are rolled out first, and then all departments (including Sales) localize their objectives to support some or all of the overall company objective. This is important to call out, as this exercise of connecting Sales goals to Company goals helps define the focus of OKR's. 2. The localizing of company objectives should generally just change the wording of the Objectives to ensure they align, but the big rocks that sales should focus on are typically in the following categories * Building a High Performance Sales Culture (hiring, ramping, setting a high bar for execution, focus on improvement of the culture) * Building Pipeline * Deal Execution - win rate, competitive win rate, utilizing resources more effectively to improve results, closing bigger deals/more deals * Executing new strategies to increase deal size, improve velocity, or open up new markets to increase TAM. Under those big rocks, you'll need to define the KR's that get you there. They need to be measurable, a stretch but achievable, and simple to track. This is harder than it sounds - but the process of refining these helps you gain that clarity. This is where you can really lean into intentionally setting up cross-functional goals, and align the support of the company to help Sales achieve their Objectives. A few examples: * If the goal is getting more customers in an industry - one KR could be to sign up 3 current referenceable customers for case studies. This aligns sales and marketing to build assets so you have more stories and social proof to help you sell into this industry. You could then have an additional KR on how many net new customers you are closing that quarter in that industry. * If you're looking to increase ACV as part of a Deal Execution objective, often there is a KR related to selling add-on products. You could align with the Product & Solutions Engineering teams to produce more assets, custom demo environments, or a new Guru card to improve sales' ability to sell this feature. Paired with an attach rate goal, this can be a powerful combo. * If there is a Culture objective, and you have a Culture survey in your org, addressing one of the key items that has been flagged by the team is a great way to show commitment towards improving the environment. For example there could be a new tool that addresses a major gap or point of friction for AE's. Setting roll out dates with RevOps that map to improved productivity is motivating to the team. While every company is different, sales Objectives are going to generally fall into one of 4 major categories outlined above. These need to be mapped to the company Objectives, and then it's important to lean into the benefits that the OKR process provides when defining KR's. Clarity in how to hit your Objectives. Visibility across the org of the key strategies you're leaning into the hit your Objectives. Cross-Functional alignment to get all teams rowing in the same direction to achieve shared Objectives.

Moving from a Manager to a Director means that you have the skillset to not only take action on tasks or initiatives given to you, but to be the one that provides the strategy and vision that creates the initiatives and tasks. Being proactive in identifying risk or future problems, thinking through possible solutions and what is best for your business, employees and customers, is key to moving from managing to directing. As a Director, you become more concerned with the broader business outcomes and how your team(s) impact those outcomes, as well as you take ownership in providing insights to the business to influence and determine the strategy. You can start to build these skills as an individual contributor. Don't wait for a leadership opportunity to learn when to speak up and provide information that can help the business, don't wait for someone to call on you to help solve a problem. Be proactive, think broader than your job, and be willing to do work that you're not compensated for to achieve the overall business goals.

Be clear on your sales methodology and discovery best practices, there is several simple tools to use from BANT ( Budget Authority Need and Time ) to Situation, Pain, Impact, Critical Event, and Decision. Generally, a sales rep needs to have a conversation with the customer to move the lead from an MQL to SQL and should have identified Pain points to be able to sell them a solution, identify the criteria for a effective discovery call and use training tools to review with your reps if this is not a SQL and not just " happy ears " 

If an account executive is sharing feedback (positive or negative!), here are a few questions you can ask to decide how to incorporate it. 1. Is the feedback specific? To act on feedback, we have to have enough information to properly diagnose the cause. If an AE shares that an account was unqualified, did they share the name of the account and the particular reasoning? 2. Do we know what led to the feedback? To act on feedback, you have to know what to change. Identify the specific behavior or process that led to the feedback. In this case, perhaps there was a qualification question that wasn’t asked or we had incorrect data in the CRM about the account. Different causes require different solutions and we shouldn’t assume the cause. 3. Is this an individual occurrence or a trend? Ask if they have any additional examples for the feedback or even recent counterexamples. Scoping the occurrence of the feedback will help you figure out if you need to work with single individuals or change an overall process. Don’t treat feedback as global unless you have shown a sufficient sample size. Once you have gotten the above information, you can decide how to implement a change (and if a change is worth implementing). If the feedback seems to be coming from a one-off situation, you may want to approach at the individual level. If the feedback seems to point towards a larger trend, you may want to design an experiment or A/B test to see if the suggested changes work. Lastly, make sure to proactively request feedback from the AE team. Their input is particularly valuable for (1) deciding how to prioritize account books and (2) refining your Ideal Customer Profile and even identify new use cases. 

A mentor taught me to evaluate opportunities leveraging the VIP framework . The framework incorporates three inputs Vision, Impact and People. Here is a quick breakdown of how I have thought through each of the inputs. 1) Vision: How excited are you about the companies vision and mission? How aligned is the leadership team and company around the vision? Does the company have aspirations of being a generational company solving a large problem set? 2) Impact: Is there an outsized opportunity to drive impact for customers, the company and the people I work with by leveraging my experiences and skillsets? 3) People: Do the folks I'll be working with share similar core values? What is the quality of the leadership team and personnel? What can learn and develop from their experiences?

This is a good, and interesting question. Like many of the other questions, answering this properly requires more context, so I'd ask that you DM me to find some time to chat. A couple of questions that come to mind when reading this question include: How similar or different are the ICPs for these two products? What are the ACVs of the products? How do their sales cycles compare? Are your product and marketing teams investing in both of them equally? Etc. While many might know Vanta as automating SOC 2, we have many products that our sales team sells today, and all of those products are pretty complex (the world of compliance is about as subjective as it gets). One thing that we've seen in asking reps to sell multiple products is that they're going to focus on the products that are easiest to sell, and the products that will make them the most money. The art and the science here is being really thoughtful around pricing and packaging methodology, and also sales compensation incentives, so as to drive the results that you're looking for. Once again, hard to answer this one directly without more context, so please reach out to me directly!

There are many ways to crush your sales interview, but an excellent sales interview usually comes down to 3 core elements -- #1) Preparation #2) Storytelling 3) Self-Reflection. The best candidates I've interviewed will always come PREPARED to: * Answer why they are interested in the company and the role * Answer what they know and don't know about the industry/role (having thoughtful questions for your interviewer shows you're curious and eager to learn) * Pitch the service/product you're trying to sell (assuming this is a quota-holding sales role) But it is not enough to come prepared, you must also showcase your STORYTELLING skills. Selling is storytelling at its best, and the best way to highlight your strengths is through concise and effective examples from the past to show, not tell your interviewer how you're qualified for the role. Here are some stories (real-life examples) you should have in your back pocket: * Think of a time you successfully overcame an obstacle (how did you do it?) * Think of a time you unsuccessfully overcame an obstacle (what happened and how did you deal with it after?) * Think of a time you worked collaboratively with teammates or other teams (what worked well and didn't work well in that example?) * Think of a time you had to resolve a conflict or misunderstanding between a client or colleague (what approach did you take?) Remember that true storytelling means painting a picture for the interviewer of what you would be like in certain scenarios. So be sure to do more than just give an example -- be sure to explain why this story is important and what you learned from it. Try to always tie the lesson back to a relevant skill for the role. Finally, the ability to SELF-REFLECT can help you stand out from the crowd. Everyone always talks about how great they are in an interview, but not everyone has the self-awareness to speak about their areas of development. We all have things we need to work on. So the more aware you are of the good, the bad and the ugly that you may bring to this role, the more you appear to be self-aware and coachable. Here are some good self-reflection questions: * What may some challenges be for you in this role, and more importantly, how will you address them? * What is your plan to ramp up and set yourself up for success when you start? (What is your 30/60/90 day plan?) * What are one or two things that may set you apart from all the other candidates? What is your secret sauce? * How will you stay motivated in this role during difficult times? Do you have examples of self-motivation in the past? If you can come PREPARED, STORY-TELL and SELF-REFLECT in your interview, you will surely impress your interviewer. I know I'm always looking for sales candidates who have done their homework, know how to paint a picture or highlight their strengths effectively, and be vulnerable about what they need to work on. 

When it comes to determining the timeline for involving internal stakeholders in an opportunity with a customer, several key considerations come into play. Firstly, we need to ascertain if the customer has a genuine business problem that needs solving, if there's a dedicated champion within their organization, and if they have the budget allocated for the solution. Our internal resources are valuable but limited, so it's crucial that we allocate them judiciously. My AEs are tasked with the responsibility of validating that the organization they're working with not only has the capacity but also the capability to execute before we bring in additional resources. During our forecast discussions, I encourage my team to break down the steps they'll need to take to progress an opportunity, including the internal resources required for success, and ensure that the customer is aligned with this approach. While C-suite engagement isn't typically necessary for the opportunities my team handles, we consistently collaborate with customer success, IT, product, legal, and sales engineering teams. Salesforce has a unique structure where some individuals on each selling team focus on a single product. This means that AEs often serve as the initial point of contact, investing time in understanding and qualifying the customer's business problems before involving additional resources. This approach ensures that our efforts are targeted and efficient, maximizing the impact we can make for our customers.