Great question, I've shared a response to this on LinkedIn here recently and I'll share it again here: You know they want people with a “proven track record of hitting quota”. What do you do? What do you say? Here’s your playbook: First, be up front about your metrics and be very clear: “My goal was X, I hit Y, that resulted in 82%. I closed Z number of deals, with an average deal size of $XYZ. My deal count was on point, but my average transaction size was a bit lower than where it needed to be to get to 100%. Here’s why that was the case.” You need to be explicit about the metrics, the numbers, the pipeline, the average deal size, the deal volume, throughput, and more. Doing this is going a long way to make up the delta between 82% and 100%. The hiring manager should believe you know the mechanics of success inside and out. Second, provide context about the team and your performance, NOT excuses. Find a win in there. Maybe you were in the top half of performers, or better? “There were 12 folks on my team and while I only finished last year at 82%, I was 3rd on the team, and only 13% behind number 1. The distribution of performance was as follows: half the team was below 60%, the top performer was 95%, and I was third at 82%. There were some challenges across the team as follows” Talk about why you think performance was what it was (the challenges) but don’t make them sound like excuses and don’t trash your company or former leaders. Be measured, be direct, and be fact based. Third, provide ownership, not excuses. “I thought 82% was ok performance, but my objective was to be 1st on the team, and here are 3 things that I thought I could have probably done better in that role to get me from 3 to 1” Then list those three (or however many) areas for improvement, and make sure they would be applicable to how you would succeed in this new role. You KNOW there were things you could have done better. Own them. Always close this portion with your expectations for yourself and reiterate the areas you’d be focused on to drive to 100% in this new role. The reality is that many of your peers interviewing for the same role have also been below quota, so the difference of who’s moving forward will come down to who the hiring manager BELIEVES will hit at their org. Remember, only about 42% of folks hit quota last year! Lastly, and as a reminder, please don’t lie. About anything.

Does your sales org share order/revenue budget details with you? My order/revenue targets to allow the company to meet guidance is typically very different than my quota. I use the order target information on my resume and not quota metrics unless that outcome is better for the year.

As you probably know, those roles, when you can get a great set of accounts (the 'patch') can be incredible opportunities to do very well $$ for many years. I'm not surprised you're getting hit up like you are, but maybe consider in your LinkedIn, maybe in the role description below, include something like one of the following descriptors: 1) Manage 7 of the companies largest and most strategic relationships 2) Responsible for relationship and growth of 12 strategic accounts 3) Currently own a book of existing accounts that generates ~$9M in annual revenue for our organization Sometimes roles can be ambiguous, so you can even state that your speciality is managing and growing existing relationships. Correct me if I'm wrong but you're happy where you are so really only would want to hear from these types of similar roles that you might consider even having MORE upside, so you don't worry about turning off the 'hunter' opportunities.

Excellent advice, thank you! Exactly what I needed to hear.

Well just be aware that the 'present job market' isn't great. So first of all, I'd make sure that you are very very clear on exactly what you want to do, what role you want. It sounds like it's a management level role at a large org. But first line manager (managing individual contributors) or possibly a second line manager or higher (managing managers)? Or are you ok with an IC role at a great org. I think you have some unique experience at the startup and that can be leveraged for future success for sure, although in today's market, IF you're looking at a tier 1 type of org (ServiceNow, Pure Storage, even Salesforce, etc) you're probably ok for a solid senior level IC at the AE level. Then you'd have to work into management from there. If you go one notch down (still great orgs) you can probably land in a management role. But again, it's really important to articulate specifically what you want to do and then have a crisp and clear plan for how to communicate all the things that you did in the startup and how they translate in to leadership experience.

Thanks for the perspective. My heart might lie in startups watching things grow and develop and there's more player-coach opportunity there to still benefit $-wise from individual production. And that makes your platform extremely valuable!

Hey there - the first thing that comes to mind is that job titles are just that - job titles. They are somewhat arbitrary. So I think you need to change the narrative about why your personal/prior experience doing what you've done will set you up for success in this role. What I mean specifically is that you should do some work to understand the deal dynamics (who you'd be selling to, how challenging is the sales cycle, what steps are involved) and then show that you have something similar in your past, you've done deals with a similar complexity, even if only a few? For example if your current deals are like $30k, but your largest is $60k, you can talk through how much you enjoy that are are looking to consistently work with those types of deals. Do you have any customers that have a similar profile (organization size, industry, etc) as those that you'd be selling to. Have you sold to a similar profile (i.e. director of finance, head of HR, etc). There's a lot of angles you can take to not generalize the 'scope' of a deal!

Great advice! Although I meant more so not increasing the scope of deals. Rather if you are an AE, or BDR manager - managing a team of 6 reps. How do you apply for a role where youd be going for snr.manager or head - managing managers etc.

Ah, managing managers. My best advice would be you need to have built a very strong, repeatable process for managing your ICs, and one that has resulted in success of your team. What you're looking to do in your next role is to take THAT playbook, and apply that playbook to other managers. So the important ingredients are: 1) You have built the playbook yourself (of course much of it may already have been bulit and you've been trained on it - but you've made tweaks and made it your own) 2) Your team has had success. While the success is important, what you're really selling is the process or playbook. I.e. the reason WHY my team has had success is because this is our specific recipe for the role. (this includes your sales process, your hiring process, your performance management process, your meeting cadences, your deal reviews, your 1/1 strategy and cadence, EVERYTHING) 3) So then you parlay that into "We KNOW this playbook works really really well, and we need to take it from 1 team of 7 ICs to 5 teams of 35 ICs". 4) Then the gold is when you run the ROI of having your performance applied to the teams that are underperforming your team - how much of an impact that will have, from a math/numbers/deals/revenue standpoint. All that to say, if your team is underperforming now, I'd pump the brakes on trying to build that empire with more teams :)

In short. No. You are considering your career prospects and making the right moves it sounds like. Congrats on the success thus far. The way you explained this transition to me, assuming it does go through and happen, is really exactly how you should explain this transition to any hiring manager in the future, and they will respect it. Especially if you're hitting quota (leave out the 'just barely' part LOL).

To be clear when I said 'no' I meant: "No, it's not too soon to leave".

Remote roles are definitely not dead! That said, the more junior your sales role, the more likely you’ll be asked to be in the office, which makes sense. If I’m hiring a new SDR team, I want them in the office 5 days a week. To learn how to work professionally, to hear other calls, to get the vibes going, and to have appropriate oversight and management. On the other end of the spectrum is the enterprise seller with years of experience chasing larger deals - they can be remote and most orgs just want the best talent regardless of location. You have to earn that though, and mid level AEs will likely have some kind of office presence (hybrid even) would be my expectation given current macro and hiring conditions.

Ok, outside of all the insights you can hear on RepVue, you can and should look at the following: 1) All the funding history of the company, when did they raise capital, have they raised capital (we'll be incorporating this into RepVue too in the future!) 2) History of headcount changes (you can see some of this here too) i.e. have they had layoffs in the past, how many, what caused them? 3) What are the new product releases they've done, do they do PR, etc on those- read that if they do 4) It may seem invasive but you're tying half of your income to the company in terms of variable compensation (if that makes sense) so ask some tough questions of the leadership like 'why do we lose deals', 'what is the cash burn of financial outlook'. 5) Engage with current and former employees too via backchannel and see if they'll have a conversation with you - it happens all the time!

Well as a start-up founder myself, I can tell you that grit and resiliency are traits that you absolutely possess. So I think you really need to lean in on: 1) The experience you have as a big tech IC seller in your earlier career 2) The STORY about how you transitioned over to your startup and how that's completely aligned with your next role (you hit on it - fundraising is like enterprise sales, you were personally closing $50k deals, you know how to handle the board room conversations, how to manage multiple stakeholders, etc) Also the buck stopped with you. 3) Is going back to big-tech a good idea? Well as you know there are challenges, but if you can land a role with a top tier org, the cash comp (which you highlighted as a priority) can be big. Again though, you'll need to do some storytelling here, which I bet you can. Be excited about how you can leverage that experience to completely OWN a territory or book of accounts (kind of like how you have to OWN all outcomes in a startup).

Thank you! That’s a great input. Off to the races!

Well it's not just you LOL. On the sales hiring meter right now I'd say the following: 2018-2021: "I don't care what background they have, please get them in that AE seat ASAP" (Oh and pay them whatever) 2022-2023: "How much will it cost us if we fire two thirds of our sales team?" We've literally seen both ends of the spectrum in the past 5 years. There's also a saying you take the elevator down but the stairs back up. This means that over the past year or so we've been slowly climbing the stairs back up to a better hiring environment. There was some headwinds coming with AI, although I believe that was more precautionary, and then bam the uncertainty of the tariffs hit, and if we had climbed from the first floor to the 5th or 6th of a 10 story building, this put us back down maybe to the 2nd or 3rd. The thing about where we are now is that we're not yet on the elevator. I think tariff uncertainty will be a reasonably short lived thing and in a couple more months we'll be back on the climb. But to your question, as of right now. Today. It's tough.

It's tough because right now the hiring market is a bit dry in SaaS - BUT I expect that to only last a few months or so. So let's assume that it opens back up. I believe the long term earnings upside in a SaaS / tech sales role is going to be higher than it is in med device, although with med device you're not quite as subject to the economic macro whims (my impression from speaking with folks, I've not sold them personally). I think you hit the nail on the head though in terms of exploring both. I think leveraging your experience to transition into a tech/software sales role that has some healthtech exposure will be your best bet to get your foot in the door but you need to carefully research the product and territory/book of accounts to make sure you can be successful. I don't think it's feasible to jump into a top tier SaaS company right out of the gate, but once you've got your first role you can parlay that a couple years. On the med device side of things, I don't know the industry as well in terms of the players (outside of the big ones) but it would seem you could parlay your current role into a stronger org or territory with more earnings upside. This is a bit of a long ramble, but my recommendation would be why not kind of pursue both options in parallel?

Yes, start with and AE role; that’s the play. Couple other things to consider: 1) You’ll likely need to lean on your earlier selling career vs. your recent leadership experience during the process (both getting an ‘in’ as well as during interview 2) Numbers are still numbers and that’s very important in tech/SaaS AE roles. So even though you were in a different industry, have a clear communication plan on how you were metrics driven in your prior successes. 3) Like almost everyone else says, getting some networking to get a referral can be gold in these situations 4) Pivoting from a lesser known tech brand to a better known tech brand is way easier than pivoting ‘cold’ into a great tech brand, so consider just getting your foot in the door in tech without shooting for the moon (ServiceNow, Salesforce, Snowflake, etc) right out of the gate.

Thank you sir! Two additional quick ones for you... I have SNOW experience from an old role and have been trying to parlay that into a role there, and have had some referrals, however no luck. Does it matter the number of referrals that are in the system, as in - is that a knock against a candidate if they keep striking out? And 2, is there any value to go network in Vegas for SNOW's Knowledge 25? Appreciate the feedback in advance.

In my experience, start-ups are much more likely to take a flyer on someone with no SaaS/tech experience. I went from a director of sales in the chemical space to a Senior Enterprise AE at a start-up. Less ego at most start-ups, where making sure you are a cultural fit is as important as your relevant experience. If you can click with a founder, they won't care nearly as much on SaaS vs general sales experience.

$150k. Ha just kidding. I actually posted about this on LinkedIn just this week. We get asked by sellers all the time how do I move up from $150k to $300k (or some other reasonable delta) and it comes down to deal complexity. The data I shared showed the average compensation based on deal sizes and frankly when you think about your next sales role, you should absolutely be considering the size of the transaction as a key driver for compensation. Also we typically recommend incremental steps to get to $300k (or similar). In other words, if you're at $150k OTE now, your deal size might be $25K, $35K, in ACV. So for your next role, parlay that into a $75k transaction size. There will be slight increases in the complexity of the deal of course, but not so much that they would immediately eliminate you from the process. If you try to go from $25k deals to $350k deals, you won't make it through the process (or probably even get an interview tbh). And the reason is that you have to uplevel your selling game for that size of deal. They can navigate multiple senior or executive level stakeholders, they are typically going to be presenting on site, they are navigating procurement, compliance, legal; they are coordinating multiple internal stakeholders as well.

Got it. Thanks for this!

Oops. Posted my reply in teh wrong spot.

I think the question is not as complicated or controversial as some make it out to be. I don't necessarily propose asking for a 'live' copy, I recommend asking for a 'template' of the comp plan. What you want is to understand the structure. Take this example: "As a seller I love the ability to overachieve and am used to having a large portion of my compensation tied to my performance. Can you share the structure of the variable compensation plan or a template so I can make sure I understand how I'll be measured and what key elements will drive success in the role?"

Things were heading in the right direction I think broadly over the past few quarters from the disastrous 2022 / early 2023. With some of the market uncertainties, that immediately impacts the top of the market, big spending public companies, and all that over time potentially trickles down, so we're absolutely seeing the following: 1) Companies are just slighly pumping the brakes on massive hiring initiatives but we're still seeing general hiring trends continue to be ok but not great, some hiring has come off the board though 2) Some deals are temporarily slowing down and being paused from a spending perspective. The CFO is not comfortable committing RIGHT now during this time of uncertaintly. My personal belief is that this will be fairly short lived, and we'll get back to 'gradual improvement'. We won't get some massive bounce back though, just back to generally improving sentiment. I just can't see the tariff uncertainty lasting more than a couple months. It's not to say the actual impact of the tariff policy won't play out over some time, but right now we're kind of in this time where we really don't know what the actual policy will be long term.

Nah, I wouldn't overthink it too much to be honest. I think it's totally fine to have a side business listed on your LinkedIn. That said, is the side business in ANY way relevant to success in the core role that you're trying to attain. If it's not, you could consider leaving it off, but if it involves any type of deal making, or really anything close to being relevant, I would leave it on there as it shows you're a self starter, etc. I think, unfortunately, people believe things like this are the 'cause' of why they haven't been able to land the role they're looking for recently, when in reality the overall macro job market is probably way more to blame. As to your second point, I would really lean in on a hybrid approach, like 'I've sold "Snowflake, Celonis, Immuta" through this agency and have loved the technical aspect of it and want to parlay that into my next role being exclusively on the software side. Based on the current market conditions though, you may have to take a lesser tech brand or earlier stage company to 'get your foot in the door' in pure software but once you do that you can then move up the stack to a better known brand (based on your success).

Honestly I think that the SDR role has always been somewhat at risk of automation, but not specifically like 'AI agents' or robots. First of all, many people forget that it's illegal for an ai based agent to do an outbound dial without consent (and I don't know too many people that are giving consent LOL). So if there's going to be outbound calling it will be a human. Then you need to ask will that practice still exist 10 years from now. Hard to say but probably. But all the other mediums still exist. I think the next generation of SDRs will need to be a bit more technical to handle all the tools and AI enrichment and all the other buzzwords and stuff happening in the industry. So my current take (subject to change) is that we will continue to have SDRs for the foreseeable future. They will need to be more technical. They will be pushing out way more messaging across various mediums, which will make it EVEN HARDER to get attention, and so the cycle begins again. LOL ok that's stream of consciousness. :)

Ok I've seen this many many times and I typically say that you'll likely always want to get to that enterprise role. So it's really more about timing. Consider: 1) How many more years can you crush it in mid market. I always hate walking away from a bird in the hand so to speak. How is your territory or book of accounts evolving 2) Are people crushing it in enterprise like you are in mid market - I'm going to assume the earnings ceiling is higher but is it WAAAAY harder to get there. 3) Once you get to enterprise, even if you're only doing 95% vs. 150% in mid market, you are now "IN" and could potentially parlay that enterprise role into a different organization that's potentially a big step up in terms of the brand and the upside, so that's kind of the long game. 4) When you are at a company and in a mid market role BUT were also promoted to enterprise in that organization, that's a massive green flag for external hiring managers. Massive. So in summary, make the money while you can in your current role, watch to see when it might dry up, when you have the opportunity to move to enterprise, do so, and then go from there.

Well I’m assuming that this is coming from an SDR. It’s an unfortunate question, and the reason I say that is because you should ALREADY know what the parameters are for getting a promotion. When you start your SDR journey, there should be clear parameters of ‘Here’s what it will take to get into position to be considered for an AE role’. Maybe that’s hitting a number 8 out of your first 12 months (non-ramped), maybe it’s something else. But I would always look for this information way before you need it. Also this allows you to work towards specific, measurable targets.

Got it. Thanks for this!

I'm definitely, 100% bullish on the future of tech sales. Here are some considerations: 1) AI will help automate prospect research and some top of funnel operations work, you still have to do the selling. It will also make product moats harder to come by. I like brand as a moat, network effects as a moat, and data as a moat (notice a theme of what we focus on at RepVue haha?) 2) Get good at using AI in your process and get good at talking about it, those in HS now will be selling in 6 to 8 years and they are growing up with it. 3) Human interaction with smart and capable sellers will be at a premium in the future.

Hey there. It's an interesting question and my primary response would be no, nothing is 'standard'. Not sure if you've seen this but in the RepVue survey we actually are asking our SDR users HOW they are primarily measured. Here are the results from March 2025: 16.1% of SDRs are measured based on activity 22.2% of SDRs are measured based on scheduled meetings 25.1% of SDRs are measured based on CREATED opportuntiies 36.7% of SDRs are measured based on CONVERTED opportunities Some of the decision depends on the size or complexity of the account - for example I would prefer that if you get the right persona of a very strategic account on the phone, you really want to have your enterprise AE on that initial call. And this would maybe be a scheduled meeting measurement type of thing. I don't really like activity based measurement really. But for an SMB type deal if the company does use SDRs (that's debatable whether they should) I'd probably tend towards converted opportunities. In any of these scenarios I also like some kind of small kicker for closed won business too!

Thanks Ryan! I'm operating purely outbound in the SMB/LMM segments, whereby the sales cycle is longer, and the conversion rate between initially booked meeting and sales qualified opportunity is very low. Perhaps this adds context?

Then what you are describing from a compensation plan is not abnormal. I don't have all the details but of course leadership is balancing the impact of filling the calendars of AEs with non-qualified accounts. But like I said there's always a balance.

Really varies by the organization. My take is that if there is meaningful upsell opportunities, then a 'seller' should be involved in that. Sales pros (AEs) really are different personas than CS roles. If there is a lot of long term upsell opportunities you could structure this a couple ways: Option 1: The seller lands the new logo and has 1 year to upsell and they get full credit for that upsell, and a CS person 'overlays' and is responsible for typical CS stuff and renewal Option 2: The seller lands the new logo and transitions the new logo to a CS person immediately who is charging hard after upsells. Seller goes back to hunting only. In this case you're really not looking for CS people you're looking for more account management / account director type roles. Option 3: This could be like option 1 except the sales person is always engaged not just a period of time like a year. In this case the CS person could get some comp or credit for creating opps closed by the seller, almost like an SDR type of thing, but they're also measured (primarily) on renewals. Hope this helps!

Hah, yeah broad question but couple tips: 1. When you get in the seat, find the top sellers and listen to all their calls, study them relentlessly. 2. If you have ANY metric, like activity, etc just do whatever you can to hit that metric, and then understand the mechanics of your funnel really really well. 3. ASK ASK ASK - ask as many questions as you can - check your ego at the door - ask your manager, top performing peers, leadership, etc. Be a sponge. Especially about the product and market.

Sounds like you are doing the right things so far. First it's really important to be super active with your job search. When you do get interviews, consider the following: 1. Yes be honest about the challenges at your most recent stint but try to pivot as much as possible to talk about the GREAT things that happened and that you accomplished early in your career. 2. Be VERY clear about what you're looking for next - you should be leveraging the positive AND negative experiences to guide your conversation and be able to communicate that you've LEARNED a lot from those experiences and have very good clarity on what type of environment would be a good fit for you. 3. Then you need to find the common ground with what you've researched about the place you're interviewing and the type of environment where you'd thrive - and really really focus on that. Good luck!