Get answers from sales leaders
Alicia Lewis
Culture Amp Senior Sales Director • January 12
Being in sales, we experience challenges on a daily basis. One of the bigger frustrations is having a great quarter or year and then seeing the dial goes back to zero, knowing you need to start all over again. It’s what we all sign up for, but that doesn’t make it any easier of a pill to swallow. As a sales leader, one of the biggest challenges can be motivating reps to maintain consistency. Keeping reps motivated to successfully climb the mountain each quarter is not a one size fits all approach. For some reps, it’s providing growth and development opportunities that keep them driving, for others it’s SPIFs and recognition that helps them get where they need to be. Finding a way to effectively manage your time can be another big frustration. At times, the sheer number of responsibilities on our plate can feel overwhelming. It’s hard when everyone seems to need something from you and there aren't enough hours in the day. I’ve found that it’s important to be as highly organized as possible, prioritize tasks, learn your productivity patterns, block out calendars to complete important activities and schedule breaks to refresh.
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Shahid Nizami
Braze APAC Vice President of Sales • January 10
The biggest reality of sales is that you are as good as your current quarter. No matter how well you may have done in the previous quarter, the meter comes back to zero at the beginning of the new quarter/new year. I have been in sales for more than 2 decades and have seen numerous quarter ends/month ends. The trick to avoid burnout is to ensure that you disconnect from work every now and then. I try to take 5 days off every quarter to re-energize myself and get back on the grind. I also keep on taking up a new hobby which also is a great way to destress yourself without having to go on a week long holiday. At present, I am learning how to play the guitar :)
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Roee Zelcer
TikTok Head of Sales, Products & Services • February 9
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.
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Brandon Love
Salesforce Regional Sales Director • October 11
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.
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Brian Tino
AlphaSense Director of Strategic Sales, EMEA • January 25
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.
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I always recommend that candidates study the job description carefully. Take a look at the qualifications and skills/experience that the hiring manager wants. Do your best to come up with examples/stories to showcase those desirable skills/experiences in the interview. If you have time, it never hurts to connect with someone who is doing the role today and pick their brain on what they like, don't like, and do to succeed in the role. You should be able to find them on LinkedIn. This type of insight is invaluable as you will be learning from someone who is doing the job you want. If you're talking to a cross-functional partner that you're not as familiar with, get curious. For example, I really appreciate it when candidates take the time to ask me, "how can I make your life easier in this role? how can this role help contribute to your team?" This type of question is a launchpad and invitation to discuss future collaboration opportunities. Remember it's just as important for you to evaluate if this role or company is a right fit for you as it is for the hiring manager and company to evaluate if you are a right fit for them. So be sure to throw in one or two questions to help you evaluate your decision as well.
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Sarah Mercedes (Osborne)
HubSpot Head of Corporate Sales, West Coast • January 24
Sponsors are critical for career progression. When you think about the best persons to lean on for sponsorship, you should be thinking about someone who is already bought into you and would endorse you to others within the business. You want to also ensure that this person is well connected and has a "voice at the table" that you don't have a "seat" at yet. Then, you need to ask that person for their support. Most importantly, you then need to create value and as mentioned in another response, ensure the things you are working on and focused on to create value align with what is important to the business and will create impact at scale.
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Charles Gryor Derupe
accessiBe Director of Enablement • February 7
Great question! There are three specific ways I do this: 1. There are some annual reports done for Sales Enablement that come from third-party sources like Forrester and Gartner. These may be gated, but sometimes they are sent by tools vendors. 2. Use your tool vendor resources! I always ask my CSMs for all the tools we own if they've created an annual trends report or a "best practice' doc for their specific tools whether it's outbound tools, content engagement, knowledge, etc. They have these for their own product/core marketing behind gated sites but since you're already a customer, they should be accessible to you without the barrier. 3. Forums - one I follow is the Sales Enablement Society forum where professionals ask questions. And, I guess we should give Sharebird a shoutout too!
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Eric Martin
Vanta Head Of Sales • November 28
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!
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George Cerny
Iterable VP, Growth Sales, B2B2C Sales & LATAM • November 15
"You can't improve what you don't measure" - Peter Drucker. When starting out in a new market, there can be lots of uncertainty. This uncertainty is the starting point, however, for a fun and exciting journey to figuring this new market out. But uncertainty can be the enemy of action, so you want to remove as much uncertainty as possible, as quickly as possible, so you can get out there and start driving results. A few places to look for data in the planning and early implementation phase to eliminate uncertainty: 1. Your network - while you may not have a network of people in this new market already, you should be able to define a couple people who would be willing to speak with you who can help get the ball rolling. One or two quality conversations with your network can lead to a number of intros, and increase your network size overnight. If these people already know you, they'll also be kind if you fumble through your first conversations or have some misconceptions going in. 2. Interviews - when I was opening the Latam team, I learned so much from the interview process. I spoke with dozens of the top leaders in the industry and the vision became more and more clear each conversation I had. They helped me calibrate the resources needed for success, nuanced buying characteristics in each country that I was unaware of, partners and strategies that I wouldn't have learned about without their expertise, and more. I approached the process humble, and was honest about where I was at in my journey of learning the landscape, and so many people were happy to help fill in the blanks. 3. Online research - there's no shortage of information online. This is an obvious step and a great place to get a baseline before you test it out in the wild. This can get you past the initial uncertainty phase pretty quickly, and put you in a position to take action. That action COULD be to hire someone who IS certain and can go build out the appropriate KPI's based on their vast expertise in the the new market you're looking to enter. If this is an option and makes sense for your business - then this is a short answer. Go hire a superstar and let them do what they're great at. Get them what they need and get out of the way. If that's not the appropriate action, then you need to establish a baseline to measure against - so you can improve and re-calibrate along the way. A few things I would consider in going through this exercise: 1. Prioritize winning early, over winning BIG early. You want to prove concept, validate the mission and get people fired up for the cause early. You want positive visibility across the org, and an infectious enthusiasm in this new market. If you shoot too high, do a good job, but don't quite hit your big lofty goals, you'll move slower, dampen the enthusiasm of the team, and may even get skeptics on if it's the right bet. Set very attainable goals, crush them, and ramp the goals up quickly from there. 2. Think long-term revenue, short term activity. The short term revenue will come as a natural output from intense focus on activity. As stated there will be some uncertainty early on - especially around when/where/how that first deal will come in. So instead of overanalyzing it - go out and get data. Lots of data. Set intense activity goals and talk to as many prospective customers as possible. Don't overqualify when you still aren't positive what you're qualifying for. Every conversation is valuable early on. If you hit your lofty activity goals, and have a solid product market fit, you should naturally hit reasonable revenue goals in the first year. Year 2 is really where you want to ramp up expectations after validating assumptions in year 1. 3. Re-calibrate, re-calibrate, re-calibrate. Every week you should review what we learned week over week. Trends, competitors, partners, what's resonating, what's not, resource needs, etc. Your ICP will likely fluctuate during this time, which will inform the types of prospects you'll want to go after. You may adjust this as often as weekly early on. This is also where you review your achievement against your baseline metrics, and may adjust these KPI's if they're not the right ones. But you need a starting point. TL;DR When entering a new market you want to eliminate uncertainty as quickly as possible so you can take action. Hire or network with top talent in this new market to improve your ability to define starting KPI's that make sense. Prioritize high activity and achieveable revenue targets early to collect more data and build momentum. Re-calibrate often based on your initial KPI's and adjust as you continue to get real data about your product in this new market.
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