Brian Tino

In my experience, two of important KPIs that most sales teams miss are: * Number of purposeful conversations * Number of experiments And it makes sense because both of these metrics harder to 1) define and 2) measure over time. However, if done well they can be can be two of the biggest unlocks and fastest ways to progress a developing go-to-market motion. Number of Purposeful Conversations Many sales teams measure number of contacts sourced, outreaches made, calls/demos completed, etc. While these metrics all help better understand the economics of your sales funnel, they all miss the context of the conversations your team is having (ie. the quality). In order to measure "purposeful conversations", first you need to define what that means for your organization and sales motion. Each company may define "purposeful" slightly differently, but ultimately it needs to be a conversation in which both parties were engaged, explored problems that your solution could solve for the customer, and lead to an honest discussion about the viability of your product or service helping that customer's specific pain points. If there are tweaks or additional critieria you need to add on to customize the definition for your organization, go for it! The next step is to determine how you’re going to measure it. Usually I've seen this done as a new "Activity Type" in Salesforce (or whichever CRM you use). It requires training your team on what qualifies/does not qualify as a "purposeful conversation" and then enablement on how to properly log it in your CRM. By orienting your team around this type of a metric, it unlocks the quality of conversations and gives you as a sales leader the opportunity to probe in more deeply with your reps to understand why certain conversations were purposeful while others were not and allows you to begin to see patterns to focus your efforts towards generating more purposeful conversations. Number of Experiments Whether you’re first getting started and in the early stages of validating product-market fit, identifying your ideal customer profile, or refining your sales motion; or even as you mature as an organizion and are looking to move into Enterprise, launch new products, or break into new markets...experimentation is critical. To find the right recipe for success, you're likely going to need to test different personas, outreach techniques, messaging, narratives, objection handling, etc. The more experiments your sales team is able to run, validate in the market, learn from the results, and share those learnings, the faster your sales team is able to find success. Work with your team to build a light weight framework for tracking & documenting the experiements you have in flight. At the very least, make sure you capture: * What you want to test? (Hypothesis) * How you plan to test it? (Experiment) * What did you learn? (Learnings) * How those learnings will affect your next experiment? (Next Steps) If your sales team gets great at documenting your go-to-market experiments & learnings and is able to scale the number of experiments running at anyone time, there is no greater unlock to your velocity. 

When you are the first sales leader at a company establishing the function, you're going to constantly battle the demands on your time. Personally, I tend to use a mixure of the Eisenhower Matrix combined with ruthless diligence of writing down my Top 3 priorities for the quarter, the week, and the day. By being able to quickly take stock of my Top 3 priorities across each of those 3 time horizons, I can quickly determine the importance of other asks as they relate to those priorities. Unless there is an important task that is immediately urgent, I'll strive to complete my Top 3 daily priorities before I tackle any other projects or tasks. That way, I know regardless of what the remainder of the day has in store, I was able to move forward on the most important work. Typically, I've found as a sales leader, I tend to focus my priorities across these 3 areas ranked accordingly: 1. People - most important is the investment in your people & culture that you create. Diverse hiring, providing personal coaching & development, promoting inclusive belonging, demonstrating empathetic leadership, etc. all result in disproportionate leverage across the other 2 areas 2. Customers - second only to your people is your customers. Meeting with them directly on a weekly basis, helping your team manage deals & relationships, and delivering value needs to always be a focus 3. Operations - finally, setting up the operationing structure for your team to execute within. Everything from defining your buy/sell process, building sales playbooks, refining reports & dashboards, etc. all contribute to an environment of consistenty & excellence Any other demands of your time that do not fall into one of those 3 areas need to be Scheduled, Delegated, or not done at all.

Good question! Taking a sales function up market in an existing business can be one of the most challenging but lucrative transformations of an organization. Often in the early days of your business and go-to-market motion you'll tend to focus on smaller, more nimble customers to validate your product-market fit and refine your go-to-market approach. During this phase, your supporting business structures of product development, finance, legal, security & compliance, etc. will mold to fit the requirements of your business at that point in time. Wayne Gretsky famously said, "I skate to where the puck is going to be, not where it has been." So, when it's time to go up-market, one of the most important things you need to do first, is help your supporting business structures evolve to meet you where you are headed, not where you are. To do that... 1) Be clear on your objectives - what does success going up-market look like in the next 90 days. Advice: be modest in your expectations, as it usually takes longer than you would have initially anticipated, and focus on the next 90 days at a time 2) Identify the gaps & be explicit about the resources you need - within your existing supporting business structures, what is required for them to evolve to meet you where you are headed? * Product development - are they prepared to adjust the product roadmap to the needs of larger clients? what is the mechanism for recieving, triaging, and prioritizing those requests? * Finance - are your finance policies & systems prepared to be flexible to more customized payment terms? do you have a process for completing vendor set up forms? * Legal - do you have the resources to negotiate MSAs, DPAs, security terms, etc? do you have proper policies & documentation in place to ensure compliance with GDPR, CCPA, etc? * Security & compliance - do you have the necessary policies & procedures? do you have the certifications required by the new market you are serving (ISO 27001, SOC2, FedRamp, etc.) ? do you have a process for completing security questionnairs & audits? 3) Up-level your team - going up-market can sometimes mean you need different skills, experiences, and roles within your sales organization to best support your larger clients. Begin to as yourself questions like: * Does my existing team have experience selling into larger organizations? or do I need to recruit additional talent? * Do we need to re-segment our accounts into new territories and books of business to create better alignment? * Does our current structure support a more mature selling motion? or do we need additional resources (customer success managers, accounts managers, solutions consultants, etc.) to take it to the next level? * How do we develop the skills of our team and implement a more mature sales motion with concepts like territory & account planning, champion building, business case generation, etc? 4) Join as many customer conversations as you can - by getting in the field yourself, you are able to develop an intimate understanding of the common objections & gaps within your offering or go-to-market motion, and you can provide your reps more relevant direct coaching 

Good question! When it comes to motivation, at any stage & maturity of a sales organization, you need to make sure: 1. Purpose - your sales team understands the mission & objectives of the organizations, feels connected to the purpose of what you are trying to acheive, and most importantly, can see how their work directly impacts progress towards company goals 2. Compensation - your sales team is well compensated and that the components of that make up compensation (base salary, variable inventives, bonuses/accelerators, equity, etc.) all work together to reward the behaviors required to acheive the output the company needs 3. Development - you are continually investing in the growth of your people. All top performers want to continue to learn, grow, improve, and ultimately master their craft. Look for those opportunities to expand the experience of your team, be generous with your feedback, and invest in coaching at every chance you get. That said, as companies & teams scale, the mechanisms & resources you have to impact motivation also evolve. Early Stage Companies & Less Mature Sales Organizations are usually focused on trying to find product-market fit and build a go-to-market motion to support it. During this phase, compensation plans need to be simple, aligned more to behaviors than outcomes, and reward progress. There is generally a greater need to ensure alignment and connection to "Purpose", and leaders should create opportunities for their salespeople to engage with cross-functional executives, influence the product roadmap, etc. If you are looking for a first compensation plan for your SaaS sales team, Jason Lemkin's framework can provide a great starting place. Mid-to-Late Stage Companies & More Mature Sales Organizations can then evolve to dedicate more resources to invest in their salespeople in different ways. Things like more formal career pathing, mentorship, and management development courses become table stakes. Salespeople will have opportunities to work with larger companies, build bigger deals, and raise their skillset. And compensation can shift to allow for additional rewards and incentives through SPIFs and President's Club.

Good question! I evaluate every sales candidate who is interviewing to join my team on the same 3 criteria: 1. Sales Skills & Knowledge - key expertise & skills required to be an effective salesperson (ex. conversation generation, discovery, relationship building, business case construction, managing a closing process, etc.) 2. Core Behavioral Competencies - the characteristics that can contribute to success as a salesperson (ex. motivation, presence, adaptability, coachability, etc.) 3. Alignment to Company Values - the main values we expect to be shared by all employees within the organization That said, there are aspects that tend to separate the GREAT from the BEST sales candidates. As a I reflect back on the VERY BEST salespeople I've worked alongside and had the opportunity to lead throughout my career, each of them also embodies the following: 1. Intellectual Curiosity - an innate curiosity of the world. Individuals who are deeply facinated by people & relationships, the problems or challenges they may be facing, and have a perpetual hunger to continue learning from others. These individuals tend to be the best at truly understanding a customer's objectives/pain points which enables them to provide the best solutions. 2. Resilience - formed through tremendously challenging experiences outside of their career. Each of the best people I've worked with has done something incredible in their lives before I met them. They've had success in the face of adversity. By being able to acheive their goals amidst chaos, they learned how to maintain focus on the most critical behaviors, keep themselves above the line, and weather the headwinds. These individuals tend to be the best at managing through the biggest downsturns of a life in sales. 3. Leadership - not operating behind a title, these indvidiuals embody the truest aspects of Leadership. Always putting the team's development & success above their own self-interest, these individuals find opportunities to innovate within their sales motion, and go out of their way to share their learnings & best practices with the team.

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.

Quota attainment & revenue will always the most important outcomes of any sales organization. However, the most mature sales organizations can align on a set of KPIs that will serve as leading indicators to success. It’s not to say that consistency hitting KPIs will guarantee achievement of revenue goals 100% of the time, and similarly it’s not to say you cannot meet or exceed revenue goals if you miss KPIs. Sometime all it takes is you being in the right place at the right time with one lucky well-timed deal to hit your quota. However, if your goal is to be a consistent Top Performer across a longer time horizon (years, decades, your career), well constructed KPIs should serve as a benchmark and enable you/your teams to take more complex goals, like revenue (which relies on a series of coordinated outcomes to achieve) and breaks them into the repeatable inputs that are in your control. By clearly defining & measuring the behaviors, frequencies, and competencies that combined will result in success, and controlling those aspects you can control, then on average you will be able to be able to predictably and repeatedly out perform your targets. 

One of the most important ways to help you stand out during a sales interview is to come into that interview well researched & prepared on the following: * The company & product * The interviewer * Your personal narrative * Relevant questions 1) Researching the company & product - be clear you understand what the company stands for, how they make money, and what value they deliver to clients (and be able to articulate it). You can usually do this by: * Reviewing the company website (especially blog posts, customer stories, and case studies) * Researching the company missions, vision, and values (usually in an "About Us" section) * Look at their social presence on Twitter, Instagram, Youtube, LinkedIn, etc. what are they posting about? * And if they have a free or trial version of the product, sign up for it & use it yourself 2) Researching the interviewer - get a feel for the interviewer's career path, their role & experience at the company, and what they personally care about. You can do this by: * Reviewing their LinkedIn profile to see prior work history & history with the current company * Check out social media Twitter, Instagram, YouTube, LinkedIn to see what they are posting about, and if they have written any blog post or articles themselves * See if you have any mutual connections and if you can do some back-channeling ahead of time 3) Preparing your personal narrative - make sure you have your professional story, what you want in your next role/company, and why you think you'd be the right fit for this specific role/company nailed: * Be able to tell the story of your professional journey, why you made the changes you made, and your track record of success along the way * Speak with conviction about your own personal values and what you are looking for in the next role/company (it's important there is mutual fit) * After reviewing the company, job description, and expectations, be able to speak to why do you think you are the right fit and what you can uniquely bring to the position 4) Preparing relevant questions - as an interviewer, I often get more from the questions a candidate asks because it can often provide insight into their own research & preparation, values, curiosity, and interest in the role/company: * Prioritize your questions based on what is most important to you (you'll likely only be able to get to a few of your questions in the first interview, so make them count) * Ensure the questions are relevant to that specific individual (executives will have a unique perspective on the company strategy & future, while potential peers & cross-functional partners can share more about the day-to-day and company culture) * And NEVER say you don't have any more questions (as this signals you are not well researched enough, aren't curious, and/or don't care about the role/position) Finally, as a BONUS TIP - always "close" on a sales interview by understanding definitive next steps and if the interviewer has any concerns or hesitations following your conversation

From my experience, most candidates coming into an interview put their best foot forward and perform well, however, here are some of the most common pitfalls before, during, and after a sales interview... 1) Lack of Preparation - candidates who have not done even surface level research on the following is a massive red flag: * The company - reviewing the website, blog, etc. to understand what we do * Myself and the other interviewers - looking at the LinkedIn/social presences of those who they are meeting with * The job itself - reading & understanding the job description, and * The product - signing up for a free trial if there is one and at the very least understanding the basic value proposition 2) Lack of Narrative - being able to effectively tell your personal story & professional story is critical and usually one of the first questions asked during an interview ("So tell me about yourself"). Not only does this give the interviewer a deeper understanding about your career & the decisions you've made along the way, but it also gauges your ability to effectively craft a narrative. Make sure you practice it over & over, until you have it just right! And also make sure you can articulate what you are looking for in your next role/company, and do not be afraid to be explicit about it. If the role/company isn't a fit, it's best to identify & address it early. 3) Not Following Instructions - usually this comes up during a role-play, demo, or craft demonstration, but I can't tell you how many candidates have ended up falling out of the hiring funnel for not following instructions in a prompt given during later stages of the interview. Hint: if there is something you don't fully understand or is vague around the expectations that have been asked of you, then make sure you contact the recruiter or hiring manager to get clarity. 4) Asking Non-Relevant or No Questions - typically at the end of an interview, there will be an opportunity for you to ask your questions. Make sure those questions are relevant to the person you are speaking with and avoid asking questions you could easily research on your own ("so what does the company do", or "who are some of your competitors", etc.). Non-relevant questions signal a lack of research, preparation, and engagement. And worst of all is asking no questions at all! 5) Not "Closing" at the End - especially for a sales role, I expect candidates to be willing to ask hard questions and "close" at the end of a call. If you are not able to ask questions like the following, then how could I expect you to ask hard questions & close with a prospect or customer: * "So after meeting with me, are there any questions or concerns you may have outstanding?" * "Is there any reason you would not feel comfortable recommending me to move into the next round of the interview process?" And at the very least make sure you are clear on the expectations, next steps, and timing of the remainder of the interview process. 6) Not Following Up - at the end of every sales conversation, there is an expected follow up recapping the discussion & making explicit the next steps. The same is true for an interview. Call me old school, but if a candidate does not follow up with me after an interview, it's a signal they are not engaged, or worse, not capable of crafting an effective follow up message. The hand-written note is a thing of the past. If you have my email address, send me a message and if not (or you're just looking for another touchpoint), then connect with & message me on LinkedIn.

Personally my favorite interview question, which I ask all of my hires from SDRs/BDRs to Sales Directors, is: "Of everything in your life (professionally, personally, academically, athletically, artistically, etc.), what do you consider to be your greatest accomplishment?" Of the hundreds of times I've asked this question, I've received so many incredible answers. Some people have talked about the accomplishments of building a family, qualifying for the Olympics, summiting mountains, changing careers, moving to entirely new countries and starting from scratch. All were great, and the reality is, there is no one "best answer". To me the reason I love asking this question early in an interview process is, I get to: * Quickly learn more intimate details about someone's life to begin to understand who they are as a person and discover what they value * Listen attentively and observe how they tell a story they are passionate about, and * Use that answer as a jumping off point to probe into other attitudinal & behavioral competencies From that simple question, you can then take the conversation into so many follow on questions like: * What were some of the biggest obstacles you needed to overcome to achieve that accomplishment? (which gets into the topics of resilience & adaptability) * If you were to re-live that experience again, knowing what you know now, what would you change? (which addresses self-reflection and learning) * Now that you've accomplished [insert accomplishment], what are you setting your sights on next? (which uncovers ambition & motivation) I'm curious to hear from you...what do you consider to be your greatest accomplishment?