Get answers from sales leaders
Eric Martin
Vanta Head Of Sales • November 29
As the first GTM hire and sales leader at Vanta, hitting our weekly revenue target was the absolute most important thing that I could do for myself, for the company, and for my CEO. Yes, you read that correctly, I had a weekly revenue target that I had to hit (and that we exceeded on a weekly basis for the first few years). Why weekly? I think it came from some YC guidance. :) If you're taking on a first sales leader role where there are literally no sellers, it's critical that you first roll up your sleeves and prove (on a repeated basis) that you can close deals and hit the revenue targets. Once you've established that you can get the job done, it'll become obvious to you when it's time to start scaling. And if it's not obvious to you, it might be obvious to someone else, like your CEO. To put yourself in a position where you're ready to start adding bodies, be sure to not overlook investing in key systems (i.e. buying your CRM) and processes (i.e. creating an AE hiring loop). If you're taking on a first sales leader role where there are already butts in seats, your primary responsibility is still to hit the number, whatever it takes. Rather than immediately rolling up your sleeves and learning how to close a deal (though this is something you should prioritize), you might instead start by doing an audit of the sales org that you're joining. Doing an audit should help give you a better sense of how strong (or weak) of a position you and the team are in to hit the revenue targets. My advice, communicate up (to your CEO) your findings as they come, and with full honesty. As the CRO of Snowflake once told me, "Sales leadership is a single elimination tournament, if you miss your number, you should expect to be replaced." It's a bit extreme, but it's also not wrong.
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Alicia Lewis
Culture Amp Senior Sales Director • April 25
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.
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George Cerny
Iterable VP, Growth Sales, B2B2C Sales & LATAM • November 16
By far the most over-hyped KPI is total pipeline created. This is certainly a key metric to track week over week as a health check, but it provides little insight into what's actually going on. The problem with total pipeline created, is at no point should the conversation end with that KPI. If it's low - why? If it's high - why? Was it one large opp? Was it a bunch of baby opps? Was it quality pipeline? Was it from one AE/Segment/Business Unit - or is everything firing on all cylinders? At best it provides directional guidance to tune into major variances and inspect. At worst it provides false confidence in a pipeline that won't get you to goal. Typically addressing total pipeline creation falls into one of two camps: 1. Mention & move on. These are meetings where the metric is called out, compared to last week and it's either * Good - "great job, let's see if we can stretch this 10% higher next week" * Bad - "we really need to prioritize pipe gen this week. Get on it." 2. Paralysis by analysis. These meetings show the metric, and then dive into 40 slides with individual permutations of how everything performed over the past week; leading to information overload and very little insight into what actually needs to change. This is why instead of just tracking total pipe creation - we want to take a three-pronged approach: 1. How are we tracking towards our pipeline generation goal (which is a leading metric against future bookings)? 2. Identify the factors that are contributing to the current results. 3. Define strategies to optimize the path to goal The standard discussion described above hits the first objective, skips number 2, and the only strategy is often "do more." We could write an entire post on steps 2 and 3, but here are a few variables that can take your basic "total pipeline creation" reporting to the next level * # of opportunities created & average opportunity value. This controls for the one big opp skewing results. You generally want more big deals, but don't want to have to rely on only one big deal to hit the goal. This helps monitor quality & quantity. * Split by region/segment/AE's - this allows you to identify people and parts of the business that are doing well and understand why (do more of it, share learnings, double down). It also ensures that those who aren't doing well don't hide behind overall success of the business and get neglected. We want to identify why they're struggling, and ideally get them unstuck to improve performance. * Pipeline by opportunity source - attribution can lead to some sticky conversations, but tracking where the pipeline is coming from is necessary to improve the overall output. This isn't meant to start a blame game, but you can't optimize something you don't measure. So if AE's, SDR's, Marketing, Partnerships, or PLG is slacking - what can we do about it? If something is working incredibly well - how can we do more? * Pipeline conversion metrics - how is the pipeline that's coming in converting through the funnel to closure? Are disco to demo conversion rates improving, declining or staying the same? What about win rate? Any new trends where we should ride the wave? Anything that's not working which we should stop doing? These metrics will give you a much deeper understanding of the factors that contribute to current results and lay a strong foundation so you can define strategies to help optimize results. With a strong team and partners in marketing, partnerships, SDR and RevOps leadership - you're a brainstorming session away from having your best pipeline generation quarter yet.
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One of the key attributes I like to test for in interviews is the candidates self awareness and grit. My favorite question to ask here is "What is the most difficult feedback you've received professionally? How did it shape your career?" The quality of the answer demonstrates the candidates ability to internalize feedback and take action.
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Nick Feeney
Loom VP, Revenue • March 10
As mentioned earlier, KPIs vary depending on the business and teams specifically. Below are a few metrics that I find businesses neglect to prioritize: * Employee satisfaction * Retention * Burnout and mental health are critical topics managers should be maniacally focused on * Manager call reviews (Gong, Chorus) * Managers should be constantly providing constructive feedback and hearing more from the customers' voice in order to improve performance and sales motions * Delineating engagement by location and persona * Far too often I see leaders report total metrics without the proper insights into trends by geo, title, etc. * Discounts * How often are you bringing in revenue at your list price? * Are we losing deals due to costs? Budget? * Why, how, and when are we discounting and how does that impact the business? * Proposals sent * I’ve seen frontline managers assume that their reps have sent a quote or order when a buyer has reached a certain stage. Never assume. * SLA * How long does it take for your inbound team to follow up with a lead? * What percentage of leads are followed up with? * How quickly do your AEs follow up via email with a summary from a discovery call? * Meeting acceptance rate * % no shows * % conversion by title and location * Conversion rate * Lagging and leading indicators/trends * Opportunity lifecycle * % of opps by stage * Length of stage progression * NPS * Promoters vs. passives vs. detractors * Customer lifetime value
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Brandon Love
Salesforce Regional Sales Director • October 12
Navigating tactical opportunities within our enterprise accounts is a challenging but vital aspect of my role. My team focuses on deals that align with our clients' strategic objectives. On average, each AE handles 3 to 5 opportunities per month. While many of the key stakeholders remain consistent (sponsor, procurement, key decision maker), the diverse nature of our products means managing these deals can be intricate and time-intensive. Understanding each product and its customer-centric benefits is crucial. This insight allows us to align and prioritize opportunities effectively. Once consensus is reached, establishing a mutual close plan with specific steps and responsible parties becomes much smoother. When execution is spot-on, and the product's benefits are acknowledged, quantified, and a timeline is set, the rest of the sales cycle shifts towards project management and ensuring accountability, rather than traditional selling. This approach ensures that our efforts are laser-focused on delivering value and driving outcomes for our clients in line with their strategic vision.
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Shahid Nizami
Braze APAC Vice President of Sales • January 10
In today's world it is relatively quite easy to make a very well informed decision when assessing a new role in a different company. These are some of the things I look at and advise my mentees to do too : * If it's a public listed company, look at their financials to figure out their year on year growth. * Check out websites like RepVue which give you a very good understanding about how sales reps in that company are doing * On LinkedIn, check out the trend on their headcount,especially in sales, is it increasing consistently or not. * Check out analyst reports and websites like g2.com to see how the product is rated by their customers. * Check websites like Glassdoor to understand about the culture of the company you are considering * If possible speak with a few customers and partners of the company as well.
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Some questions I like to ask are: * Tell me about a time you missed your goals. What happened? (Answer should explain why the person missed goal, what lessons they learned from it and how they've been performing since) * What is a piece of critical feedback you've received from a client, colleague or manager in the past? (Answer should show the person's ability to be coached and take action on feedback) * Tell me about a time you had to re-motivate yourself during a difficult time. How did you do it? (Answer should show the interviewer what the person is motivated by and how they continue to keep themselves motivated when they encounter roadblocks in the role) * What approach would you take in the first 30/60/90 days to ramp up? (Answer should show how the person is thinking about setting themselves up for success. Are they just depending on onboarding and training to get them there? Do they have other ideas on how to prepare for success?) * What is something you don't enjoy doing? Can you give me an example of what your pitch for this thing would be? (How the person reacts to this spur-of-the-moment exercise is very telling. Are they able to go with the flow and think on their feet? Are they able to reframe their thinking?)
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Grant Glaser
Salesforce Director, Sales Leader Excellence Coach • January 11
There needs to be a problem to solve. Begin by finding out what problem exists. Then, * Create a clear problem statement * Define the current vs. desired future state * Outline KPIs/metrics you want the program to impact * Build an MVP to shop around with sellers & sales leaders * Ensure you have sponsorship & buy-in from your sales leaders & teams * Deliver the program * Capture feedback * Iterate & repeat
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Charles Gryor Derupe
accessiBe Director of Enablement • February 8
I think the easy answer here is "buy-in" from your leadership. But what does this actually mean? They can say it, but that doesn't always mean that they'll prioritize or even fund it for growth. The approach of top-down is 100% the way to go in my experience but here are a few tactics I and my peers have used to reinforce this: 1. Get DRI's from leadership to support key initiatives and ask from top-leads who they would recommend to be assigned to them (frame it as "career growth opportunities"). Collaboration on top projects means that they have a vested interest in seeing it succeed as they're also putting hours into them. I wouldn't depend on them for building the initiative content per se, but they can certainly give good feedback and support on comms and accountability. 2. Communication! Do you have the right, centralized channels where all enablement content is available? But, do you have these paired with something they need daily such as product launches or process updates? 3. Speaking of communication, share your results with leads and cross-functional partners. Proving effectiveness (both objective and subjective) creates the belief that it's worthwhile to invest in, even if it's just giving attention. This could include weekly updates of quarterly business reviews. 4. Make it fun! I know that budgets are somewhat strapped, but prizes for participation work well. I often hear competitions are also good, but unless it's tied to making them something that helps them close deals faster or get some kind of reward (like a spot in annual President's Club-type incentives), I usually find it ends in just fun.
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