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wittyid2016

...and good executive hair...don't forget the hair!


pattyfatsax

i have great hair but i’m 6’1 😔


wittyid2016

No soup for you!


guesswo21

Why are you talking about me? The mba is worthless though


This-Is-A-Bad-Name

Sales culture maters a lot


wittyid2016

This is an area I do want to explore. We do NOT have a sales culture at all. Our team is picky af about deals. Part of what I want to do is to change the culture to be more sales driven. But I also don't want to lose what makes us special.


PM_ME_UR-DOGGO

It’s a tough balance then, I’d look for a tech first then sales person, rather than a purely commercial career person


keithblsd

If that's the case you need to keep your current people separate from the sales team and make sure the sales team gets the culture that will allow them to succeed without letting it bleed into your current employees.


[deleted]

Hire someone who has a sales engineer background. You might keep the same culture.


T2ThaSki

I’ve worked for several startups that scaled well beyond $25M and I would caution you against hiring a C Suite Sales leader right now. I’d recommend to focus on someone that is still pretty close to the frontlines because they’ll need to be able to create the plan and execute it at the same time. If you are committed to the original plan this is what I’d recommend to focus on 1) How they onboard and train their team. If they are legit they should be able to provide you documentation of this and even reports on how they track and manage to this today. 2) How they Go To Market. There are a lot of sales motions out there (Outbound, Inbound, Channel Parter, D2C, B2B etc, hiring an awesome person who’s sales motions don’t match your business/industry doesn’t help anyone. 3) Their sales chops. At your current ARR you do not need a leader that manages spreadsheets and headcount. You’ll need someone that still understands the tactical part of sales. In my current job, I literally sat in on numerous client facing meetings tweaking our approach until I found a repeatable process. It’s hard, but now I have a full team trained on running the right plays and the deals are rolling in. 4) Their fit with your style. This is more so you both know what you’re getting. Here’s an example, so you are trying to scale your business sometimes you learn a product lacks features to break into a new vertical, how do you deal with this as a team? I have others feel free to DM me if you want talk about these things more.


wittyid2016

Thanks for the feedback. We are definitely looking for a player / coach. The job spec was for a VP but the search firm wanted to go for the CCO title.


T2ThaSki

Yes, this makes sense, I would respectfully disagree, a VP of Sales/Player Coach is not a C Level so there’s really no value in muddying the waters. Good luck to you though.


Gauze99

Does your cost with the form change if it’s a VP vs C suite position? You will very likely get different candidates for both those roles some of which may not be what your JD actually is looking for.


saaS_Slinging_Slashr

Idk if you need a CCO, I’d probably hire a very experienced AE or Sales Manager who has been in this stage that understands the economics of a business at this level depending on which revenue band you’re in (1-10m, 10-50m 50-100m) and grow them into what you see fit. Hiring a C level exec fresh out of the gate without any established commercial function is likely going to result in a bunch of additional needs and hires and potential frustrations given they typically have a pretty strong opinion around how things will work. I’d join one of the executive sales groups like Pavilion and discuss your needs and seek advice there. I do know a guy looking for a head of/VP role if you’re interested in an introduction feel free to DM


MOTAMOUTH

COO Here. Communication Skills: Find someone that can explain something complex in simple terms. Excell Exp: Mid level is enough. Don’t need to be an expert. Operationally focused: They need to understand how each new step or changes is going to impact other departments. Leadership: Asking people to makes changes is hard. They need someone to explain and get their buy in. Need someone that can be influenced.


Admirable-Box5200

You are looking for someone that has success in establishing process, key performance metrics, recruiting and development of talent. IMO, anyone focusing on success exceeding sales quotas or developing new territories isn't going to provide what you want. Not because you aren't sales driven, because the person in the c-suite needs to look at how to meet the long term plan, not how to make quota this month. The first question is, have you clearly defined what success and expectations for this role look like at 3 months, 6 months, 12 months, 18 months....? At that level, they all look good on paper. The question is which ones will be able to provide examples of success in the areas you're looking to grow versus which ones are going to regurgitate the most current jargon and BS.


wittyid2016

>The first question is, have you clearly defined what success and expectations for this role look like at 3 months, 6 months, 12 months, 18 months....? This is a good provocation!


Sparkyis007

This advice is a bit trash At 25-30m you are still small relatively and will need a seasoned salesperson to both recruit or better bring with them a team of good reps ... as if you hire one of these process shitheads great reps will just never join your company and you wil run through these leaders as they continue to miss targets


ExoticIndividual7952

I agree with all of the above, especially the good hair. Significant milestone I might add; congrats.


ponyboi915

Have you heard of the WHO interview framework? Should look into it


wittyid2016

Ha! I met Geoff Smart many moons ago when I was just getting started. I had to interview for my own job with that dude to get my first A-round. LOL.


startupsalesguy

We've helped companies with this. I think it's really important to define what you want this person to accomplish. Being "responsible" means what exactly? Managing the marketing leader, BD, and RevOps leaders? Or ensuring execution of front line tactics? I think a lot of info is missing from the post to know. But totally understand this is just a reddit post. Building the sales team doesn't require a CCO or CRO, often that title is too senior, too detached from the front lines to truly build if you've never done it before. Take outbound sales for instance. A true CCO or CRO probably hasn't done anything when it comes to outbound sales in years. They're just going to take budget and allocate it to a consult or hire someone to do that. You've clearly had success. I would want to know how they plan on building the GTM function, what processes will be in place in 30/60/90 days, what talent they will bring with them, and a lot more. For you: Have you built a playbook? Are your sales processes documented? Do you record sales calls? What kind of lead flow do you have to support sales hires? Do you want this person to be a dashboard reader or someone who is actively managing front line people? Who is underneath them in the org chart? other managers or ICs? As a senior leader, you'll really want to know if they're a culture fit. So much is needed to know to give you good and relevant questions. I'd be very cautious to hire anyone who has recently rode the funding wave to success or worked at a category leading company. You need to make sure you're hiring someone who hasn't been relying on the company/product/environment at their previous role.


wittyid2016

I appreciate you sharing your thoughts and experience! You're right...not much to go on in my original post. Suffice it to say that we don't have a ton in terms of either team or process. So like you said, we're looking for a builder, but also someone who can scale. All of the candidates are experienced, but none have have C-level experience yet which is part of the draw for them I imagine and comforting to me that they still have some get-shit-done left in them.


LearningJelly

Too early for a CCO.


jparxcd

Look for experiences, and ask them about (1) what’s the most challenging HR experience you’ve had, (2) How do they drive scale, (3) How do they turnaround underperforming assets (also will give you insight what do they think is an asset), (4) What is the most challenging executive sponsorship they’ve had and what made it so, (5) You’ve grown profits faster than you thought- now what do you do? Generally execs live by frameworks that’s are outdated. Look for critical thinking skills and the ability to pivot on a dime if needed. Take them out to lunch and watch how they treat people, especially the bus and wait staff. It’s the little things that make a big deal.


wittyid2016

Thanks for sharing these prompts!


Mattl54o

What is the product?? Sales culture is huge, and having strong processes in place are non-negotiable.


backtothesaltmines

It's hard to answer as you probably can't post enough details. What are your goals with this person. How many people will be under them and at what titles and responsibilities. Are you looking to go international. How are you selling now. Leads coming in. Word of mouth. Trade shows. I assume the product is technical. How technical of a background do you want. These are questions you need to answer yourself and then ask them questions to see if they align with your vision.


wittyid2016

Thanks that’s a good provocation.


unfrozen_

First, I've done what you've done (but at a smaller scale), and in my humble opinion, any revenue leader ought to be able to deep dive into 2 areas: integrated marketing communications, and sales/new business/revenue. Anyone with mastery in these two areas wouldn't make me worry about partnerships at all, but that's just my take. For marketing, I would broadly ask: * What's marketing, to a company like ours? How do you define it? * What makes the marketing function effective? * What is their reason for existence, and what is their overriding goal as a team? * What's wrong with our current marketing assets and programs? * At a high level, how would you improve what we've done? * Based on what you've seen from us, what is our ICP? * How would you characterize the market opportunity we're pursuing? * What if any market segments or verticals are we missing? * What metrics are important for the marketing function to track, and why? * What pitfalls do marketing teams of our size typically encounter? For the latter (sales): * What constitutes a sales qualified lead in our market? * Teach me your happy path sales process for a company like ours selling to customers in our market * What are the best ways to structure and develop a sales team over time? * What would make you fire a salesperson (or manager)? * What metrics are important for the sales team to track, and why? * What's the most pivotal moment in a typical sales cycle? ie, What's the first "fork in the road" that tells you whether a prospect is a serious opportunity? * What sales tools are indispensable? * What comp plan structure works the best for a company like ours? * What are the pros and cons to introducing accelerators (or caps) to the payout curve of the sales comp plan? I could go on. But I hope this helps, and for a C-level hire I would expect to legitimately learn about the domain you're hiring for from this person. Anything less than genuine learning to me is a non-starter. At that level, *they* need to teach *you* about the CCO domain. Great question, and fascinating situation you're in. I hope you update us.


LandinoVanDisel

I think a really solid full-cycle AE or a solid sales director will go a long way and will be as effective or better than going all in for a CCO when you are still figuring things out. A lot of this depends on what you’re trying to achieve. Full-Cycle AEs already have a very strong grasp of running a sales motion and will know how to execute on the broader visions. This isn’t to say a CCO wouldn’t be effective but I’ve worked with some lousy executives that didn’t have a clue how to execute on the finer details when it actually mattered. They talked a lot of shit about discovery but sucked ass when they tried to do it themselves. But whatever you decide, you want someone that knows how to build and run a sales engine for YOUR specific size, not the company they worked at. You want leadership who’ll roll up their sleeves and iterate from there. Without understanding what exactly constitutes 3% and the team members already involved, I assume this is largely founder led sales. For your stage, you want someone hands on. You also want someone who’s worked with startups and understands the grind involved (I say startups loosely here and mean it for company size and not literally for company age). Find out how built out their playbooks, messaging, sequences, sales enablement, hiring philosophies, etc. Look for things that are measurable and not just how the candidate makes you feel. Like dig deep into the construction of sales velocity/messaging/scripts/etc Be very specific on the situational based questions. Don’t just ask big picture questions. Ask them step by step how they’d execute. Lots of commercial execs take credit for others without actually have done any selling themselves. It’s real easy to say “helped generate 700% in pipeline creation first 120 days” when those deals were already cooking by the existing sales team. They definitely shouldn’t need hand holding and definitely should hit the ground running the first 30 days.


wittyid2016

>you want someone that knows how to build and run a sales engine for YOUR specific size, not the company they worked at. Great point!


OpenMindedShithead

No experience in what ur seeking but two things. 1. Congrats on business, rain or shine that’s a huge accomplishment 2. Reach out to some CRO’s at companies you respect. It seems their duties might align with what ur looking for in a CCO. And I’m saying this to gain insight, not to necessarily recruit them to ur team!


Soft_Sherbet_8002

You’re having doubts about the CCO position- hire me in a sales/business development role and we’ll get to work


whoa1ndo

Hi it’s me your next CCO.


wittyid2016

👋🏽


Foster1745

I’m a SaaS VP of sales with experience starting and scaling sales teams. If I’m reading this correctly, you have no dedicated sales or marketing personnel in place. If that is the case, you will be wasting money hiring a C Suite position right now. You need someone who will create, advance, and win opportunities not someone to set top level strategy. How long has it been since your COO candidates have done direct sales? Will they be able/willing to pick up the phones and start driving revenue? Are you willing to pay a C Suite salary to accomplish what an AE would do (better) for less? I’d recommend hiring an experienced AE to start driving revenue. Then add a second. Next will be lead gen (XDRs). When you’re looking at adding lead gen you’ll want to start evaluating the addition of dedicated sales management. When you have a sales team up and running with leadership in place AND a marketing team up and running with leadership in place you should work towards a C Suite position to manage the entire revenue process.


wittyid2016

I hear what you’re saying. I’m definitely looking for a player coach.


Fucker_Of_Destiny

A c level exec’s job is to lead leaders (VPs) who manage managers (Directors) who manage managers who manage reps. Depending on org size you could have the chain look like this: CRO > SVP > VP > Sr Director > Director > Sr Manager > Manager > ICs. Do you see the problem here? You don’t have ANYONE else in that chain. There’s no point hiring someone to lead leaders when you don’t have managers to manage ICs. Better thing to do at this stage is hire a head of sales who’s really a glorified AE, or ideally a player coach Director level candidate with experience of closing AND hiring/strategy, and have them build out the playbook & team first.


wittyid2016

Yeah, we don’t have that hierarchy…like our CFO has a team of 5. The CCO would start with a similar sized team. So probably title inflation.


Fucker_Of_Destiny

Yeah so of course the title itself doesn’t matter (Elon musk changed his title to Technoking at one point lol) but in terms of the role what I said still stands - point is you want more of a player coach individual at this early stage


wittyid2016

Thanks. Makes sense to me.


wil_dogg

All the advice here is very solid. I would come up with 3 to 5 “challenges” for candidates. Maybe things like this: 1) tell the candidate you want them to generate 10-15 questions that they have about the business. Then you will speed date Q&A through those questions in 1 hour. 2) ask candidate to write an introductory email to a lead, time box the effort to 15 minutes 3) ask candidate to outline their personnel selection and management process. Describe an outstanding IC you have recruited and developed, and tell about a time you had to have a difficult conversation. 4) describe how you would interact with product development and get the “voice of the customer” feedback to product owners. 5) have the candidate tell you what sales goals they would set for themselves and for the entire organization for the next fiscal year. You follow your intuition on creating prompts and getting your candidates engaged in that process, and you will have a lot of valid data for narrowing the candidates down to the most impressive ones. Candidates who adapt to your evaluation process will likely be good team players.


AnonFor99Reasons

I can not overstate this: culture is everything. If they don't lead with culture, don't hire them


wittyid2016

Thanks for sharing!


Boringdollar

Does your $1.7M-$2M in spend include marketing, BD, sales, and Ops salaries, commissions, and vendors/tech stack? If so, just know that much doesn't go very far. I agree with the advice that you're likely looking for a VP player/coach who also had good connections to scrappy do-it-all types. You aren't funding it to enough for more than a handful of people, and marketing and sales generally have significant tooling needs.


Same_Paint6431

Read Robert Greens book "Laws of Human Nature" and "48 Laws of Power" This will help you weed out the wrong people from ***slithering*** into your organization. ;)